Benzoyl Peroxide → HCID 18986082, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred room temperature solution of 4-bromo-2-methylpyridine (1.72 g, 10 mmol) in carbon tetrachloride at was added N-bromosuccinimide (1.9 g, 10.5 mmol). The mixture was warmed at 90° C. After 30 minutes, the mixture was cooled, and benzoyl peroxide (100 mg) was added and refluxing was continued. After 7 hours, the mixture was cooled to room temperature, washed with aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 4-bromo-2-bromomethylpyridine as a brown oil [MS m/z 250/252/254 (MH+)] which was determined to be 75% pure and was used without further purification. The remaining material was determined to be 4-bromo-2-dibromomethylpyridine.

Provenance & Evidence