Phosphorus tribromide → 1-Bromo-3-(bromomethyl)-5-fluorobenzene

Participants

Reaction Steps

To a solution of 3-Bromo-5-fluorobenzyl alcohol (2.3 g, 0.011 mole) in CH2Cl2 (15 mL) was added 12.4 mL of 1.0M PBr3 (3.33 g, 0.0123 mole) in CH2Cl2, stirred for 3 hr, diluted with ether (100 mL), washed with H2O (50 ml,3×), dried over MgSO4, concentrated. Purified by column chromatography using 1:9 ethyl acetate/hexane as an eluant solvent system. 3-Bromo-5-fluorobenzyl bromide as a white crystalline material was obtained, mp 41-43° C. 1H NMR (DMSO-d6) □4.69 (s, 2H), 7.52( d, 1H, J=1.76 Hz) 7.54(d, 1H, J=1.91 Hz), 7.56( s, 1H); MS( EI): M+. m/z 266; Anal. Calc. For C7H5Br2F: C, 31.38, H, 1.88. Found: C, 31.75, H, 1.78.

Provenance & Evidence