Trimethylsilyl triflate → 1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-(benzyloxy)-phenyl)-ethanone (49.12 g; 217.1 mmol) in CH2Cl2 (750 mL) was added drop wise DIPEA (45.37 mL; 260.5 mmol) and TMSOTf (45.18 mL; 249.6 mmol), both at 0° C. The resulting solution was maintained at 0° C. for 1 h, and then NBS (42.50 g; 238.8 mmol) was added in four portions. The resulting mixture was allowed to warm to RT and stirred 1 hour. Subsequently, the mixture was concentrated in vacuo and the residue was treated with EtOAc and washed twice with water, and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chormatography (SiO2, Et2O) and crystallization from iPr2O to afford 1-(4-benzyloxy-phenyl)-2-bromo-ethanone.

Provenance & Evidence