Diethylaniline-borane → HCID 86705523, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole (0.83 mL, 1.4 mmol) and borane diethylaniline (2.5 mL, 14 mmol) in MTBE (25 mL) prepared at RT and heated to 40° C. A solution of 2-bromo-1-(3-fluoro-4-(trifluoromethyl)phenyl)ethanone (143a, 4.0 g, 14 mmol, CASRN 54429-22-3) and MTBE (30 mL) was added dropwise to the above solution and the reaction was stirred at 40° C. for 30 min. The reaction was quenched by adding MeOH followed by 1M HCl and the reaction mixture was then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (9:1) to afford 3.2 g (79%) of (R)-2-bromo-1-(3-fluoro-4-(trifluoromethyl)phenyl)ethanol (258).

Provenance & Evidence