Benzyl Bromide → HCID 10691343, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-hydroxy-4-(4-chlorobenzyloxy)benzoate (5.2 g) in dry dimethylformamide (DMF) (50 mL) is treated with NaH (60% dispersion, 0.71 g) and stirred at 25° C. for 20 minutes. Benzyl bromide (2.12 mL) is added and the solution heated at 60° C. for 2 hours. The solution is evaporated. The residue is dissolved in ethyl acetate, washed with water, dried, and evaporated. The residue is recrystallized from ethyl acetate to yield methyl 2-benzyloxy-4-(4-chlorobenzyloxy)benzoate as colourless crystals (5.1 g, 75%), m.p. 99-101° C. 1H NMR (DMSO) 3.8(3H,s),5.18 (2H,s), 5.21(2H,s), 6.7(1H,d), 6.85(1H,s), 7.3-7.5(9H,m), 7.75(1H,d).

Provenance & Evidence