methyl 2-bromo-3-methoxybenzoate

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A mixture of methyl 2-bromo-3-methoxybenzoate (0.4 g, 1.63 mmol), Pd(PPh3)2Cl2 (0.057 g, 0.082 mmol), copper (I) iodide (0.031 g, 0.16 mmol) and 3-butyn-1-ol (0.173 ml, 2.28 mmol) were stirred in trietylamine (5 ml) at 80° C. for 20 h. The solvent was concentrated under vacuum, and the residue was partitioned between ethyl acetate (15 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes:ethyl acetate 2:1 as eluent to afford methyl 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoate (0.056 g; 15% yield). MS (EI) for C13H14O4: 235 (MH+). The solvent was concentrated under vacuum the residue was partitioned between ethyl acetate (15 ml) and water (5 ml) The organic layer was dried over sodium sulfate filtered concentrated The residue was purified by silica gel column chromatography

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

実験手順: To a solution of 2-bromo-3-methoxybenzoic acid (718 mg, 3.11 mmol) in methanol (20 mL) was added a catalytic amount of concentrated sulfuric acid and the mixture was brought to reflux for 20 h. On cooling to room temperature, the solution was concentrated and the residue was taken into ethyl acetate and washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate. The solution was then filtered and concentrated to give methyl 2-bromo-3-methoxybenzoate (610 mg, 80%). MS (EI) for C9H9BrO3: 245 (MH+). to reflux for 20 h the solution was concentrated washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate The solution was then filtered concentrated

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

実験手順: To a solution of 2-bromo-3-methoxybenzoic acid (718 mg, 3.11 mmol) in methanol (20 mL) was added a catalytic amount of concentrated sulfuric acid and the mixture was brought to reflux for 20 h. On cooling to room temperature, the solution was concentrated and the residue was taken into ethyl acetate and washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate. The solution was then filtered and concentrated to give methyl 2-bromo-3-methoxybenzoate (610 mg, 80%). MS (EI) for C9H9BrO3: 245 (MH+). to reflux for 20 h the solution was concentrated washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate The solution was then filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A mixture of methyl 2-bromo-3-methoxybenzoate (0.4 g, 1.63 mmol), Pd(PPh3)2Cl2 (0.057 g, 0.082 mmol), copper (I) iodide (0.031 g, 0.16 mmol) and 3-butyn-1-ol (0.173 ml, 2.28 mmol) were stirred in trietylamine (5 ml) at 80° C. for 20 h. The solvent was concentrated under vacuum, and the residue was partitioned between ethyl acetate (15 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes:ethyl acetate 2:1 as eluent to afford methyl 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoate (0.056 g; 15% yield). MS (EI) for C13H14O4: 235 (MH+). The solvent was concentrated under vacuum the residue was partitioned between ethyl acetate (15 ml) and water (5 ml) The organic layer was dried over sodium sulfate filtered concentrated The residue was purified by silica gel column chromatography

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

実験手順: To a solution of 2-bromo-3-methoxybenzoic acid (718 mg, 3.11 mmol) in methanol (20 mL) was added a catalytic amount of concentrated sulfuric acid and the mixture was brought to reflux for 20 h. On cooling to room temperature, the solution was concentrated and the residue was taken into ethyl acetate and washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate. The solution was then filtered and concentrated to give methyl 2-bromo-3-methoxybenzoate (610 mg, 80%). MS (EI) for C9H9BrO3: 245 (MH+). to reflux for 20 h the solution was concentrated washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate The solution was then filtered concentrated