Carbon tetrabromide → 4-(3-Bromopropyl)phenol

Participants

Reaction Steps

A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield.

Provenance & Evidence