Carbon tetrabromide → 3-(2-bromoethyl)-5-methoxy-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-methoxy-1H-indol-3-yl)ethanol (4.0 g, 20.92 mmol) in DCM (30 mL), CBr4 (7.98 g, 24.06 mmol) was added, then the reaction mixture was cooled to 0° C. and PPh3 (6.3 g, 24.0 mmol) was added. After stirring at rt for 2 h, the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/hex 3:1, Rf=0.31) to yield the title compound as a brown oil which turned into a solid during storage in the freezer. LC-MS conditions B: tR=0.78 min, [M+H]+=254.06.

Provenance & Evidence