4-(2-bromophenyl)butan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

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: To a solution of 4-(o-bromophenyl)-1-butanol (1.222 g, ca 0.0053 mol) and tetrakis(triphenylphosphine) palladium (0) (650 mg, 0.562 mmol) in 1,2-dimethoxyethane (55 mL) was added thiophene-2-boronic acid (2.057 g, 0.016 mol) and 1N aqueous NaHCO3 (15 mL). The resulting mixture was heated at reflux under nitrogen atmosphere for 3 days. The dark reaction mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4, filtered through a bed of Celite and concentrated to yield a crude which was purified by flash chromatography (30% EtOAc in hexane) to yield 4-(2-thien-2-yl-phenyl)-butan-1-ol as a light brown oil. The resulting mixture was heated at reflux under nitrogen atmosphere for 3 days The dark reaction mixture extracted with EtOAc (100 mL) The organic layer was dried over Na2SO4 filtered through a bed of Celite concentrated to yield a crude which was purified by flash chromatography (30% EtOAc in hexane)

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

実験手順: To a solution of 0.4 M 9-BBN in hexane (72 mL, 28.8 mmol) was added 4-bromophenyl-1-butene (3.99 g, 18.9 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 h. The mixture was treated sequentially with 3.3 mL of 6N aqueous NaOH (19.8 mmol), THF (7 mL), and 30% H2O2 in H2O (7 mL), then refluxed for 2 h. The reaction mixture was then cooled to room temperature. The organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL). The aqueous extracts were combined, saturated with solid K2CO3 and extracted with Et2O (3×50 mL). The combined organic extracts were dried over Na2 SO4, filtered and concentrated. The resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane) to yield 4-(o-bromophenyl)butanol). refluxed for 2 h The reaction mixture was then cooled to room temperature The organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL) extracted with Et2O (3×50 mL) The combined organic extracts were dried over Na2 SO4 filtered concentrated The resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane)

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

実験手順: To a solution of 4-(o-bromophenyl)-1-butanol (1.222 g, ca 0.0053 mol) and tetrakis(triphenylphosphine) palladium (0) (650 mg, 0.562 mmol) in 1,2-dimethoxyethane (55 mL) was added thiophene-2-boronic acid (2.057 g, 0.016 mol) and 1N aqueous NaHCO3 (15 mL). The resulting mixture was heated at reflux under nitrogen atmosphere for 3 days. The dark reaction mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4, filtered through a bed of Celite and concentrated to yield a crude which was purified by flash chromatography (30% EtOAc in hexane) to yield 4-(2-thien-2-yl-phenyl)-butan-1-ol as a light brown oil. The resulting mixture was heated at reflux under nitrogen atmosphere for 3 days The dark reaction mixture extracted with EtOAc (100 mL) The organic layer was dried over Na2SO4 filtered through a bed of Celite concentrated to yield a crude which was purified by flash chromatography (30% EtOAc in hexane)

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

実験手順: To a solution of 0.4 M 9-BBN in hexane (72 mL, 28.8 mmol) was added 4-bromophenyl-1-butene (3.99 g, 18.9 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 h. The mixture was treated sequentially with 3.3 mL of 6N aqueous NaOH (19.8 mmol), THF (7 mL), and 30% H2O2 in H2O (7 mL), then refluxed for 2 h. The reaction mixture was then cooled to room temperature. The organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL). The aqueous extracts were combined, saturated with solid K2CO3 and extracted with Et2O (3×50 mL). The combined organic extracts were dried over Na2 SO4, filtered and concentrated. The resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane) to yield 4-(o-bromophenyl)butanol). refluxed for 2 h The reaction mixture was then cooled to room temperature The organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL) extracted with Et2O (3×50 mL) The combined organic extracts were dried over Na2 SO4 filtered concentrated The resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane)