4'-Bromo-2,2,2-trifluoroacetophenone → 1-(4-Bromophenyl)-2,2,2-trifluoroethanol

Participants

Reaction Steps

4′-Bromo-2,2,2-trifluoroacetophenone (3.00 mL, 19.8 mmol) was stirred in MeOH (66 mL) at 0° C. Sodium borohydride (0.748 g, 19.8 mmol) was added and the mixture was allowed to warm to ambient temperature. The mixture was stirred for 3 hours, then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was then washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (eluting with 5% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford a racemic mixture of the title compounds. The racemic residue was resolved by Chiral SFC purification (Chiral Technology OJ-H 2.1×25 cm, 5 uM Column; eluting with 5% isopropyl alcohol/CO2).

Provenance & Evidence