Benzyl bromide
A mixture of the benzyl alcohol (0.0006 mol) and 48% HBr in water (2 mL) (clear solution after 5 minutes) was stirred at room temperature for overnight (12 h). Solid precipitated out after 4 h. The reaction mixture was diluted with 50 mL ethyl acetate, washed with 50 mL aqueous saturated NaHCO3 solution, dried (Na2SO4) and evaporated under reduced pressure to give the corresponding benzyl bromide which was purified by triturating with hexanes (white solid, 74% yield).
Note: Yield increased to 92% in 0.002 mol scale.
Reference: Cassady, J. M.; Howie, G. A.; Robinson, J. M.; Stamos, I. K. Org. Synth. 1990, Coll. vol 7, 319.

Bn-Br’s some nasty stuff. Caught a drop of it on my sleeve and 15 minutes later (when I eventually got my eyesight back) my boss sent me home for the day. “You just benzylated your eyeballs.”
Useful procedure.
J
May 1, 2008 at 8:45 pm
Thanks.
pmgb
May 1, 2008 at 9:26 pm