(Diethylamino)sulfur trifluoride → Tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate

Participants

Reaction Conditions

Reaction Steps

Diethylaminosulphur trifluoride (DAST) is added under an inert atmosphere to a cold (−78° C.) solution of alcohol 39. The reaction mixture is stirred at −78° C. until no starting material is seen by TLC. The reaction mixture is partitioned between water and EtOAc, and aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine and dried over anhydrous MgSO4. Purification by flash chromatography gives tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate.

Provenance & Evidence