5-bromo-2-methyl-1-benzofuran

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (5-Bromo-2-methoxyphenyl)acetone (6.6 g, 28.6 mmol) was dissolved in methylene chloride (50 ml) and cooled to −70° C. Thereto was dropwise added a 1 M solution (28.6 ml, 28.6 mmol) of boron tribromide in methylene chloride over 15 min. After the dropwise addition, the mixture was heated to room temperature and stirred for 1.5 hr. Then, the reaction mixture was ice-cooled and water (50 ml) was added. The insoluble matter was filtered off and the filtrate was partitioned. The aqueous layer was extracted with methylene chloride. The organic layers were combined, and dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1) to give the objective compound (3.45 g, 57%) as a colorless liquid. After the dropwise addition the mixture was heated to room temperature cooled The insoluble matter was filtered off the filtrate was partitioned The aqueous layer was extracted with methylene chloride dried over anhydrous sodium sulfate The desiccant was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1)

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

実験手順: A solution of 2-[(4-bromo-2-formylphenyl)oxy]propanoic acid (5.08 mmol) in acetic anhydride (6 mL) was treated with sodium acetate (15.25 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (10 mL) and was stirred at room temperature for 20 min. The solution was then further diluted with water (50 mL) and was extracted using ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting brown residue was purified by flash chromatography (hexanes), affording the title compound as a clear oil (660 mg, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=2.02 Hz, 1H) 7.47 (d, J=8.59 Hz, 1H) 7.35 (dd, J=8.72, 2.15 Hz, 1H) 6.58 (s, 1H) 2.45 (d, J=1.01 Hz, 3H). The resulting solution was heated to reflux was stirred at room temperature for 20 min was extracted The combined organic layers were dried over magnesium sulfate filtered concentrated in vacuo The resulting brown residue was purified by flash chromatography (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-[(4-bromo-2-formylphenyl)oxy]propanoic acid (5.08 mmol) in acetic anhydride (6 mL) was treated with sodium acetate (15.25 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (10 mL) and was stirred at room temperature for 20 min. The solution was then further diluted with water (50 mL) and was extracted using ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting brown residue was purified by flash chromatography (hexanes), affording the title compound as a clear oil (660 mg, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=2.02 Hz, 1H) 7.47 (d, J=8.59 Hz, 1H) 7.35 (dd, J=8.72, 2.15 Hz, 1H) 6.58 (s, 1H) 2.45 (d, J=1.01 Hz, 3H). The resulting solution was heated to reflux was stirred at room temperature for 20 min was extracted The combined organic layers were dried over magnesium sulfate filtered concentrated in vacuo The resulting brown residue was purified by flash chromatography (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-[(4-bromo-2-formylphenyl)oxy]propanoic acid (5.08 mmol) in acetic anhydride (6 mL) was treated with sodium acetate (15.25 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (10 mL) and was stirred at room temperature for 20 min. The solution was then further diluted with water (50 mL) and was extracted using ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting brown residue was purified by flash chromatography (hexanes), affording the title compound as a clear oil (660 mg, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=2.02 Hz, 1H) 7.47 (d, J=8.59 Hz, 1H) 7.35 (dd, J=8.72, 2.15 Hz, 1H) 6.58 (s, 1H) 2.45 (d, J=1.01 Hz, 3H). The resulting solution was heated to reflux was stirred at room temperature for 20 min was extracted The combined organic layers were dried over magnesium sulfate filtered concentrated in vacuo The resulting brown residue was purified by flash chromatography (hexanes)

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (5-Bromo-2-methoxyphenyl)acetone (6.6 g, 28.6 mmol) was dissolved in methylene chloride (50 ml) and cooled to −70° C. Thereto was dropwise added a 1 M solution (28.6 ml, 28.6 mmol) of boron tribromide in methylene chloride over 15 min. After the dropwise addition, the mixture was heated to room temperature and stirred for 1.5 hr. Then, the reaction mixture was ice-cooled and water (50 ml) was added. The insoluble matter was filtered off and the filtrate was partitioned. The aqueous layer was extracted with methylene chloride. The organic layers were combined, and dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1) to give the objective compound (3.45 g, 57%) as a colorless liquid. After the dropwise addition the mixture was heated to room temperature cooled The insoluble matter was filtered off the filtrate was partitioned The aqueous layer was extracted with methylene chloride dried over anhydrous sodium sulfate The desiccant was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1)

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (5-Bromo-2-methoxyphenyl)acetone (6.6 g, 28.6 mmol) was dissolved in methylene chloride (50 ml) and cooled to −70° C. Thereto was dropwise added a 1 M solution (28.6 ml, 28.6 mmol) of boron tribromide in methylene chloride over 15 min. After the dropwise addition, the mixture was heated to room temperature and stirred for 1.5 hr. Then, the reaction mixture was ice-cooled and water (50 ml) was added. The insoluble matter was filtered off and the filtrate was partitioned. The aqueous layer was extracted with methylene chloride. The organic layers were combined, and dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1) to give the objective compound (3.45 g, 57%) as a colorless liquid. After the dropwise addition the mixture was heated to room temperature cooled The insoluble matter was filtered off the filtrate was partitioned The aqueous layer was extracted with methylene chloride dried over anhydrous sodium sulfate The desiccant was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1)

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

実験手順: A solution of 2-[(4-bromo-2-formylphenyl)oxy]propanoic acid (5.08 mmol) in acetic anhydride (6 mL) was treated with sodium acetate (15.25 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (10 mL) and was stirred at room temperature for 20 min. The solution was then further diluted with water (50 mL) and was extracted using ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting brown residue was purified by flash chromatography (hexanes), affording the title compound as a clear oil (660 mg, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=2.02 Hz, 1H) 7.47 (d, J=8.59 Hz, 1H) 7.35 (dd, J=8.72, 2.15 Hz, 1H) 6.58 (s, 1H) 2.45 (d, J=1.01 Hz, 3H). The resulting solution was heated to reflux was stirred at room temperature for 20 min was extracted The combined organic layers were dried over magnesium sulfate filtered concentrated in vacuo The resulting brown residue was purified by flash chromatography (hexanes)