Sodium Thiosulfate → tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

Participants

Reaction Steps

Dess-Martin reagant (7.8 g, 18.6 mmol) was added to a solution of tert-Butyl 3-bromo-5-[(R/S)-2,2,2-trifluoro-1-hydroxyethyl]benzoate (4.4 g, 12.4 mmol) in DCM (75 mL). The reaction was stirred for one hour and saturated aq. Na2S2O3 and aq. NaHCO3 were added. The reaction was extracted with DCM (3×) and the organic layers combined and washed with brine, dried over Na2SO4 and concentrated to dryness. Purification using automated flash chromatography (SiO2, 120 g, 0-10% MeOH(NH4OH)/DCM) gave final compound as a mixture of hydrate and ketone which was used directly in step B.

Provenance & Evidence