Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 150 g of methyl p-toluate and 195.5 g of NBS in CCl4 (1.67 L) under N2 at 50° C. was added portion wise over 30 min, solid benzoyl peroxide (5.0 g). There was no exothermic reaction observed. After heating for 2 hours at 50° C., the yellow solution was heated at 65° C. for 6 hrs. There was still some unreacted starting material. The suspension was stirred overnight at 65° C. After cooling to room temperature (r.t), the precipitate formed was filtered off and washed with 150 mL of CCl4 and the filtrate was concentrated to afford a yellow oil that solidified on standing. The title compound, containing a small fraction of starting material was used in the next step without further purification.

Provenance & Evidence