p-Bromoacetophenone → 1-(4-Bromophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Ru, R=n-Pr, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in ethanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 80° C. After the mixture was cooled to room temperature, p-bromoacetophenone (0.4 mmol), ethanol (2 mL) and a solution of sodium methoxide in ethanol (0.8 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 12 h under H2 (10 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(p-bromophenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

Provenance & Evidence