2-bromohexane

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis(2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O:hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O:hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis(2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O:hexanes) provided bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

反応条件: temp:76.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis(2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C. containing The reaction flask was immersed in an oil bath to cool filtered through a pad of celite evaporated in vacuo washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml) dried (Na2SO4) filtered evaporated in vacuo