alpha,alpha'-Dichloro-p-xylene → 4-(Chloromethyl)benzyltri-n-butylphosphonium chloride

Participants

Reaction Steps

A mixture of tri-n-butylphosphine (7 g, 34.6 mmol, leq.) in toluene (50 mL) was added dropwise to a mixture of α,α'-dichloro-p-xylene (12.1 g, 69.8 mmol, 2 eq.) in toluene (200 mL) under argon gas. The reaction mixture was allowed to stir for 12 hours at room temperature under argon, after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution. The crystals were filtered and washed several times with toluene and hexanes, then air dried: 1H NMR (CDCl3) δ0.92 (t, 9H), 1.44 (m, 12H), 2.39 (m, 6H), 4.35-4.40 (d, 2H), 4.56 (s, 2H), 7.36-7.39 (d, 2H) , 7.47-7.51 (dd, 2H).

Provenance & Evidence