Phosphorus tribromide → 4-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester

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Reaction Steps

To a stirred solution of 4-hydroxymethyl-2-(2-methylphenyl)benzoic acid methyl ester prepared in Example 331A (10.85 g, 42.2 mmol) in dry DMF (40 mL) at 0° C. was added successively lithium bromide (4.00 g, 46.6 mmol, 1.1 eq) and phosphorus tribromide (4.18 mL, 44.5 mmol, 1.05 eq) at a rate such that the temperature did not exceed 5° C. On completion of the addition the mixture was warmed to ambient temperature, and quenched by the addition of ice. The resultant solution was partitioned between water and ether; the ethereal solution was dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the title compound (13 g, 96%) as a colorless oil.

Provenance & Evidence