Triphenylphosphine → 9-Bromomethylanthracene

Participants

Reaction Steps

A solution of triphenylphosphine (16.44 g, 100.8 mmol) in acetonitrile (120 mL) was flushed with nitrogen for 20 minutes. Bromine (3.3 mL) was added and a solution of anthracen-9-yl-methanol (15.0 g, 72.0 mmol) in acetonitrile (100 mL) was added dropwise. The mixture was stirred for 2 hours at room temperature and refrigerated at 5° C. overnight. The solution was cooled to 0° C. for 30 minutes and filtered. The residue was washed with cold acetonitrile and purified by recrystallization from chloroform to give 9-bromomethyl-anthracene as yellow crystals (13.47 g, 69% yield). 1H NMR (CDCl3) δ 8.51 (1H, s), 8.32 (2H, d), 8.05 (2H, d), 7.66 (2H, dd), 7.52 (2H, dd), 5.56 (2H, s).

Provenance & Evidence