Dimethyl Sulfide → (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol

Participants

Reaction Steps

To (R)-2-methyl-CBS-oxazaborolidine (Aldrich or Callery Chemical Co, 1M in toluene, 1 eq.) at −45° C. is added BH3. Me2S (1.06 eq.). To the previous solution is added at −30° C. a 1M dichloromethane solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone. After completion of the reaction, excess MeOH is added followed by IN HCl. After warming up to room temperature, the resulting mixture is filtered through a pad of celite and silica gel and washed with 30% EtOAc in hexane. The solvent is removed under reduced pressure and the resulting oil is purified by flash chromatography (20% EtOAc in hexane) to afford (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (optically enriched).

Provenance & Evidence