Carbon tetrabromide → N-methanesulfonyl-6-bromomethylindole

Participants

Reaction Steps

A solution of N-methanesulfonyl-6-hydroxymethylindole (340 mg, 1.51 mmol, from above) and triphenylphosphine (Ph3P) (415 mg, 1.58 mmol) in 5 ml of dry CH2Cl2 was cooled to 0° C. and a solution of carbon tetrabromide (551 mg, 1.66 mmol) in 3 ml dry CH2Cl2 was added dropwise via cannula (2 ml CH2Cl2 rinse). The reaction mixture was allowed to warm to room temperature. After 4 hr, the solvent was removed by rotary evaporation and the resultant purple oil was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane) to give 290 mg of N-methanesulfonyl-6-bromomethylindole, a colorless oil which solidified on standing (67% yield).

Provenance & Evidence