Tributylamine → 4-(Bromomethyl)benzyltri-n-butylammonium bromide

Participants

Reaction Steps

To a mixture of α,α'-dibromo-p-xylene (7.0 g, 26.5 mmol) in toluene (200 mL) was added tri-n-butylamine (3.43 g, 18.6 mmol) under argon gas. The reaction mixture was stirred for several days at room temperature under argon at which time the tri-n-butylammonium salt had crystallized out of solution. The crystals were filtered and washed with toluene (3×50 mL) and hexanes (3×50 mL) and dried: 1H NMR (CDCl3) δ 0.97 (t, 9H), 1.39 (m, 6H), 1.76 (m, 6H), 3.32 (m, 6H), 4.47 (s, 2H), 4.96 (s, 2H), 7.42-7.59 (dd, 4H).

Provenance & Evidence