2'-Bromoacetophenone → 1-(2-Bromophenyl)ethanol

Participants

Reaction Steps

To a solution of 2′-bromoacetophenone (15 g, 74.6 mmol) in 150 ml MeOH under argon at room temperature was added NaBH4 (4.23 g, 0.11 mol). The reaction mixture was stirred at room temperature for 24 h then quenched by addition of water. HCl 5 N was added until pH 6-7. MeOH was evaporated. The residue was dissolved in ether and washed once with water, once with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel (eluent: heptane: ethylacetate 1:1) to yield 14.8 g (99%) of (RS)-1-(2-bromo-phenyl)-ethanol as a colorless oil.

Provenance & Evidence