2-Bromophenol → Methyl 2-(2-bromophenoxymethyl)benzoate

Participants

Reaction Steps

Methyl α-bromo-2-toluate (53 g, 0.23 mole) was added to a mixture of 2-bromophenol (40 g, 0.23 mole) and potassium carbonate (42 g, 0.3 mole) in 250 mL of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 18 hours, then heated on a steam bath for 3.5 hours. The mixture was poured into ice water, and the solids were collected by filtration and washed with water to give the crude product. An analytical sample was obtained by recrystallization from hexane/ethyl acetate (38 g, mp 73°-74° C. pmr (CDCl3) δ: 6.58-8.05 (m, 8, aromatic H); 5.48 (s, 2H, ArCH2O); 3.80 (s, 3H, CO2CH3)

Provenance & Evidence