Triphenylphosphine → 1-(Bromomethyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 912 mg (3.48 mmol, 1.2 equiv) of triphenylphosphine in 10 mL of CCl4 at 0° C. is added 180 μL (3.48 mmol, 1.2 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 500 mg (3.16 mmol) of 1-Naphthalenemethanol in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 1.5 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 10/1 as eluent afforded 670 mg of the title compound as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) δ8.18 (d, 1H), 7.83 (m, 2H), 7.63-7.38 (m, 4H), 4.98 (s, 2H); Rf =0.65 in hexane/EtOAc 5/1.

Provenance & Evidence