4-Bromophenol → Methyl 2-((4-bromophenoxy)methyl)benzoate

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Reaction Steps

Wash 15.12 gm (0.315 mole) of sodium hydroxide, 50% dispersion in oil, free of oil with hexane and suspend in 250 cc. of N,N-dimethylformamide. Add 54.5 gm. (0.315 mole) of p-bromophenol in portions as hydrogen is evolved. After gas evolution has subsided, add a solution of 68 gm. (0.3 mole) of methyl α-bromo-o-toluate in 50 cc. of N,N-dimethylformamide at a rapid dropwise rate. Stir the mixture for 45 minutes and pour into 3 liters of cold water. Separate the solids by filtration, wash with water and dry to obtain 90 gm. of crude methyl o-(p-bromophenoxymethyl)benzoate which is used in the next step without further purification.

Provenance & Evidence