2-bromo-1-iodo-3-methylbenzene

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A vial was charged with copper(I) iodide (38.5 mg, 0.202 mmol), 1,10-phenanthroline (72.8 mg, 0.404 mmol), cesium carbonate (1.32 g, 4.04 mmol), 2-bromo-1-iodo-3-methylbenzene (600 mg, 2.021 mmol) and tetrahydrofuran-3-ol (1.80 mL, 22.23 mmol). The vial was sealed and the reaction mixture was heated to 120° C. for 24 h. The reaction mixture was cooled to RT, EtOAc was added and the mixture was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (25% EtOAc/hexanes). 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran was isolated as a light-yellow oil (178 mg). The vial was sealed The reaction mixture was cooled to RT the mixture was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (25% EtOAc/hexanes)

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A vial was charged with copper(I) iodide (38.5 mg, 0.202 mmol), 1,10-phenanthroline (72.8 mg, 0.404 mmol), cesium carbonate (1.32 g, 4.04 mmol), 2-bromo-1-iodo-3-methylbenzene (600 mg, 2.021 mmol) and tetrahydrofuran-3-ol (1.80 mL, 22.23 mmol). The vial was sealed and the reaction mixture was heated to 120° C. for 24 h. The reaction mixture was cooled to RT, EtOAc was added and the mixture was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (25% EtOAc/hexanes). 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran was isolated as a light-yellow oil (178 mg). The vial was sealed The reaction mixture was cooled to RT the mixture was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (25% EtOAc/hexanes)

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A vial was charged with 2-bromo-1-iodo-3-methylbenzene (677 mg, 2.28 mmol), neopentyl alcohol (2.21 g, 25.08 mmol), copper(I) iodide (43.4 mg, 0.228 mmol), 1,10-phenanthroline (82 mg, 0.456 mmol) and cesium carbonate (1.04 mg, 3.19 mmol). The vial was sealed under air atmosphere and heated to 110° C. for 24 h. The reaction mixture was cooled to rt and diethyl ether was added. The suspension was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (100% hexanes). 2-Bromo-1-methyl-3-(neopentyloxy)benzene was obtained as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to rt The suspension was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (100% hexanes)

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

実験手順: A flask was charged with bis(triphenylphosphine)palladium(II)chloride (0.042 g, 0.060 mmol) and copper(I) iodide (0.023 g, 0.120 mmol) under nitrogen atmosphere. THF (4.6 mL) was added, followed by 2-bromo-1-iodo-3-methylbenzene (0.594 g, 2 mmol), triethylamine (2.3 mL, 16.50 mmol) and 3,3-dimethylbutyne (0.251 mL, 2.040 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was filtered through a plug of silica gel and the plug was rinsed with Et2O. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes). 2-Bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene was obtained as a light-yellow clear oil. The reaction mixture was filtered through a plug of silica gel the plug was rinsed with Et2O The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes)

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

実験手順: A solution of 2-bromo-1-iodo-3-methylbenzene (200 mg, 0.67 mmol), 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (220 mg, 0.81 mmol), sodium carbonate (214 mg, 2.02 mmol) and tetrakis(triphenylphosphine) palladium (38.9 mg, 0.034 mmol) in toluene (2.0 mL)/EtOH (1.2 mL)/Water (0.2 mL) was heated in an oil bath at 80° C. overnight. The reaction was concentrated and the resultant residue purified by column chromatography (100% Hexanes) to yield 2-bromo-3-methyl-3′-(trifluoromethyl)biphenyl. The reaction was concentrated the resultant residue purified by column chromatography (100% Hexanes)

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

実験手順: A solution of 2-bromo-1-iodo-3-methylbenzene (200 mg, 0.67 mmol), 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (220 mg, 0.81 mmol), sodium carbonate (214 mg, 2.02 mmol) and tetrakis(triphenylphosphine) palladium (38.9 mg, 0.034 mmol) in toluene (2.0 mL)/EtOH (1.2 mL)/Water (0.2 mL) was heated in an oil bath at 80° C. overnight. The reaction was concentrated and the resultant residue purified by column chromatography (100% Hexanes) to yield 2-bromo-3-methyl-3′-(trifluoromethyl)biphenyl. The reaction was concentrated the resultant residue purified by column chromatography (100% Hexanes)

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A vial was charged with copper(I) iodide (38.5 mg, 0.202 mmol), 1,10-phenanthroline (72.8 mg, 0.404 mmol), cesium carbonate (1.32 g, 4.04 mmol), 2-bromo-1-iodo-3-methylbenzene (600 mg, 2.021 mmol) and tetrahydrofuran-3-ol (1.80 mL, 22.23 mmol). The vial was sealed and the reaction mixture was heated to 120° C. for 24 h. The reaction mixture was cooled to RT, EtOAc was added and the mixture was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (25% EtOAc/hexanes). 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran was isolated as a light-yellow oil (178 mg). The vial was sealed The reaction mixture was cooled to RT the mixture was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (25% EtOAc/hexanes)

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A vial was charged with 2-bromo-1-iodo-3-methylbenzene (677 mg, 2.28 mmol), neopentyl alcohol (2.21 g, 25.08 mmol), copper(I) iodide (43.4 mg, 0.228 mmol), 1,10-phenanthroline (82 mg, 0.456 mmol) and cesium carbonate (1.04 mg, 3.19 mmol). The vial was sealed under air atmosphere and heated to 110° C. for 24 h. The reaction mixture was cooled to rt and diethyl ether was added. The suspension was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (100% hexanes). 2-Bromo-1-methyl-3-(neopentyloxy)benzene was obtained as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to rt The suspension was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (100% hexanes)

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

実験手順: A flask was charged with bis(triphenylphosphine)palladium(II)chloride (0.042 g, 0.060 mmol) and copper(I) iodide (0.023 g, 0.120 mmol) under nitrogen atmosphere. THF (4.6 mL) was added, followed by 2-bromo-1-iodo-3-methylbenzene (0.594 g, 2 mmol), triethylamine (2.3 mL, 16.50 mmol) and 3,3-dimethylbutyne (0.251 mL, 2.040 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was filtered through a plug of silica gel and the plug was rinsed with Et2O. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes). 2-Bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene was obtained as a light-yellow clear oil. The reaction mixture was filtered through a plug of silica gel the plug was rinsed with Et2O The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes)

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

実験手順: A solution of 2-bromo-1-iodo-3-methylbenzene (200 mg, 0.67 mmol), 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (220 mg, 0.81 mmol), sodium carbonate (214 mg, 2.02 mmol) and tetrakis(triphenylphosphine) palladium (38.9 mg, 0.034 mmol) in toluene (2.0 mL)/EtOH (1.2 mL)/Water (0.2 mL) was heated in an oil bath at 80° C. overnight. The reaction was concentrated and the resultant residue purified by column chromatography (100% Hexanes) to yield 2-bromo-3-methyl-3′-(trifluoromethyl)biphenyl. The reaction was concentrated the resultant residue purified by column chromatography (100% Hexanes)