6-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229. extracted with EtOAc (3×50 mL) Organics were washed with brine (50 mL) dried (Na2SO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229. extracted with EtOAc (3×50 mL) Organics were washed with brine (50 mL) dried (Na2SO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229. extracted with EtOAc (3×50 mL) Organics were washed with brine (50 mL) dried (Na2SO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (0.68 g, 3.0 mmol) and phenol (0.38 g, 4.0 mmol) in anhydrous tetrahydrofuran (10 mL) was added triphenylphosphine (1.04 g, 4 mmol). The reaction mixture was stirred at room temperature for 0.5 hour under nitrogen atmosphere. Then diisopropyl azodicarboxylate (0.8 g, 4 mmol) was added dropwise at 0° C., and then the reaction mixture was stirred at room temperature for 12 hours. After the reaction, it was quenched with water (100 mL), and the product was extracted with ethyl acetate (100 mL), dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product 6-bromo-1-phenoxy-1,2,3,4-tetrahydro naphthalene (0.73 g, 80%). 1H NMR (300 MHz, CDCl3): δ 7.32-7.20 (m, 5H), 7.00-6.97 (m, 3H), 5.27 (t, J=4.5 Hz, 1H), 2.86-2.67 (m, 2H), 2.11-1.74 (m, 4H). the reaction mixture was stirred at room temperature for 12 hours After the reaction, it was quenched with water (100 mL) the product was extracted with ethyl acetate (100 mL) dried over anhydrous sodium sulfate The mixture was filtered the filtrate was concentrated The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-3,4-dihydronaphthalen-1(2H)-one (1.0 g, 4.4 mmol) in ethanol (10 mL) was added sodium borohydride (0.8 g, 21 mmol). The reaction mixture was stirred at room temperature for 0.5 hour. After the reaction, the mixture was poured into water (100 mL) and the mixture was extracted with dichloromethane (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the pure product 6-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (1.0 g, 100%). After the reaction the mixture was extracted with dichloromethane (100 mL) The organic phase was dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229. extracted with EtOAc (3×50 mL) Organics were washed with brine (50 mL) dried (Na2SO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229. extracted with EtOAc (3×50 mL) Organics were washed with brine (50 mL) dried (Na2SO4) concentrated