Triphenylphosphine → 1-(Bromomethyl)-3-methyl-2-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 5.0 g (0.029 mol) of 3-methyl-2-nitrobenzyl alcohol and 100 mL of anhydrous acetonitrile. The reaction solution was cooled to 0° C. and treated, portionwise, with 13.2 g (0.031 mol) triphenylphosphine perbromide (Ph3P—Br2). The reaction was allowed to warm to rt overnight at which point the solvent was removed and the resulting solids triturated with 50:50 ether:hexanes. The wash solvent was filtered through a fine frit and then concentrated to give a quantitative yield (7.03 g) of the desired material as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.36–7.34 (m, 2H), 7.33–7.24 (m, 1H), 4.45 (s, 2H), 2.33 (s, 3H).

Provenance & Evidence