反应详情

A mixture of 2-chloro-5-methylbenzonitrile (10.6 g, 69.9 mmol), N-bromosuccinimide (12.2 g, 68.5 mmol), and dibenzoyl peroxide (349 mg, 1.44 mmol) in benzene (350 ml) was refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was suspended in 7:3 (v/v) hexane-dichloromethane, filtered, and evaporated. The crude product was chromatographed on silica gel (650 g) eluted with 7:3 (v/v) hexane-dichloromethane to provide 4.8 g (30%) 4-chloro-3-cyanobenzyl bromide, m.p. 55°-58° C.

1. temperaturewas refluxed 1.5 hours
2. temperaturecooled
3. customevaporated to dryness under vacuum
4. filtrationfiltered
5. customevaporated
6. customThe crude product was chromatographed on silica gel (650 g)
7. washeluted with 7:3 (v/v) hexane-dichloromethane