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

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: According to the procedure for the preparation of 73B, methyl 2-(4-bromophenyl)-2-methylpropanoate (2.15 g, 8.36 mmol) afforded 1.93 g of 74A as a colorless oil. MS (ESI) m/z 211.1 (M-OH)+.

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

Procedure: To a solution of 73B (2.34 g, 10.9 mmol) in 30 mL DMF, was added imidazole (1.11 g, 16.3 mmol) and tert-butyldimethylsilyl chloride (1.97 g, 13.1 mmol). The mixture was stirred at rt for 3 h, then was diluted with hexanes. The organic phase washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 2.00 g of 73C as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+. The organic phase washed with H2O (2×) and brine dried (Na2SO4) concentrated The product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

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

Procedure: To a solution of 73A (3.06 g, 11.9 mmol) in 50 mL CH2Cl2 at −78° C., was added a solution of diisobutylaluminum hydride (35.7 mL, 35.7 mmol, 1M in hexanes). The mixture was removed from the cooling bath, stirred 1 h, then recooled to −50° C. and quenched with EtOAc (2 mL). The reaction mixture was diluted with H2O, then extracted with EtOAc (3×). The combined organic extract washed with brine, dried (Na2SO4), filtered through a 1″ pad of SiO2, then concentrated to afford 2.34 g of 73B as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+. The mixture was removed from the cooling bath recooled to −50° C. quenched with EtOAc (2 mL) The reaction mixture was diluted with H2O extracted with EtOAc (3×) The combined organic extract washed with brine dried (Na2SO4) filtered through a 1″ pad of SiO2 concentrated

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

Procedure: To a solution of 73A (3.06 g, 11.9 mmol) in 50 mL CH2Cl2 at −78° C., was added a solution of diisobutylaluminum hydride (35.7 mL, 35.7 mmol, 1M in hexanes). The mixture was removed from the cooling bath, stirred 1 h, then recooled to −50° C. and quenched with EtOAc (2 mL). The reaction mixture was diluted with H2O, then extracted with EtOAc (3×). The combined organic extract washed with brine, dried (Na2SO4), filtered through a 1″ pad of SiO2, then concentrated to afford 2.34 g of 73B as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+. The mixture was removed from the cooling bath recooled to −50° C. quenched with EtOAc (2 mL) The reaction mixture was diluted with H2O extracted with EtOAc (3×) The combined organic extract washed with brine dried (Na2SO4) filtered through a 1″ pad of SiO2 concentrated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-bromophenyl)propanoic acid (2 g, crude) in tetrahydrofuran (50 mL) was added a solution of borane in tetrahydrofuran (1 mmol/L, 13 mL, 13 mmol) at 0° C. The mixture solution was stirred for 3 hours at 0° C., then worm to room temperature, and quenched by water. The solvent was removed, purified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1) to give 2-(4-bromophenyl)propan-1-ol as a colorless oil (1.8 g, 96%). 1H NMR (300 MHz, CDCl3): δ 1.7.38-7.46 (m, 2H), 7.10-7.13 (m, 2H), 3.72-3.78 (m, 2H), 2.84-2.98 (m, 1H), 1.23-1.27 (m, 3H). worm to room temperature, and quenched by water The solvent was removed purified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-bromophenyl)propanoic acid (2 g, crude) in tetrahydrofuran (50 mL) was added a solution of borane in tetrahydrofuran (1 mmol/L, 13 mL, 13 mmol) at 0° C. The mixture solution was stirred for 3 hours at 0° C., then worm to room temperature, and quenched by water. The solvent was removed, purified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1) to give 2-(4-bromophenyl)propan-1-ol as a colorless oil (1.8 g, 96%). 1H NMR (300 MHz, CDCl3): δ 1.7.38-7.46 (m, 2H), 7.10-7.13 (m, 2H), 3.72-3.78 (m, 2H), 2.84-2.98 (m, 1H), 1.23-1.27 (m, 3H). worm to room temperature, and quenched by water The solvent was removed purified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1)

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

Procedure: According to the procedure for the preparation of 73B, methyl 2-(4-bromophenyl)-2-methylpropanoate (2.15 g, 8.36 mmol) afforded 1.93 g of 74A as a colorless oil. MS (ESI) m/z 211.1 (M-OH)+.

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

Procedure: To a solution of 73B (2.34 g, 10.9 mmol) in 30 mL DMF, was added imidazole (1.11 g, 16.3 mmol) and tert-butyldimethylsilyl chloride (1.97 g, 13.1 mmol). The mixture was stirred at rt for 3 h, then was diluted with hexanes. The organic phase washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 2.00 g of 73C as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+. The organic phase washed with H2O (2×) and brine dried (Na2SO4) concentrated The product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)