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

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

Procedure: According to the procedure for the preparation of 73C, 77A (4.90 g, 22.8 mmol) afforded 6.51 g (87%) of 77B as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+.

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

Procedure: According to the procedure for the preparation of 73C, 77A (4.90 g, 22.8 mmol) afforded 6.51 g (87%) of 77B as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+.

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

Procedure: To a solution of 4-bromophenylacetone (5.00 g, 23.5 mmol) in ethanol (100 mL) at 0° C., was added sodium borohydride (976 mg, 25.8 mmol) portionwise over 5 min. The mixture was stirred at rt for 15 h, then quenched with 5% citric acid. The volatile solvent was removed in vacuo. The mixture was diluted with water, the pH was adjusted to 4.5 with 1N HCl, then aqueous phase was extracted with CH2Cl2 (3×). The combined organic washed with brine, dried (Na2SO4), filtered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2) and concentrated to afford 4.90 g of 77A as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+. quenched with 5% citric acid The volatile solvent was removed in vacuo The mixture was diluted with water aqueous phase was extracted with CH2Cl2 (3×) The combined organic washed with brine dried (Na2SO4) filtered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2) concentrated

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

Procedure: According to the procedure for the preparation of 73C, 77A (4.90 g, 22.8 mmol) afforded 6.51 g (87%) of 77B as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+.

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

Procedure: To a solution of 4-bromophenylacetone (5.00 g, 23.5 mmol) in ethanol (100 mL) at 0° C., was added sodium borohydride (976 mg, 25.8 mmol) portionwise over 5 min. The mixture was stirred at rt for 15 h, then quenched with 5% citric acid. The volatile solvent was removed in vacuo. The mixture was diluted with water, the pH was adjusted to 4.5 with 1N HCl, then aqueous phase was extracted with CH2Cl2 (3×). The combined organic washed with brine, dried (Na2SO4), filtered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2) and concentrated to afford 4.90 g of 77A as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+. quenched with 5% citric acid The volatile solvent was removed in vacuo The mixture was diluted with water aqueous phase was extracted with CH2Cl2 (3×) The combined organic washed with brine dried (Na2SO4) filtered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2) concentrated