反应详情

A stirred refluxing solution of 4-(4-chlorobenzoyl)-3-chlorotoluene (2.65 g, 9.99 mmol) and dibenzoylperoxide (100 mg, 0.413 mmol) in benzene (100 ml) was treated in portions with an intimate mixture of N-bromosuccinimide (2.2 g, 12. mmol) and dibenzoylperoxide (100 mg, 0.413 mmol). The mixture was refluxed 1.5 hours, cooled, and filtered. The filtrate was evaporated under vacuum, triturated with diethyl ether (100 ml), and filtered. The filtrate was evaporated under vacuum and the residue was chromatographed on silica gel (500 g) eluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph to provide 1.69 g (49%) of 4-(4-chlorobenzoyl)-3-chlorobenzyl bromide, m.p. 88°-90° C.

1. temperatureThe mixture was refluxed 1.5 hours
2. temperaturecooled
3. filtrationfiltered
4. customThe filtrate was evaporated under vacuum
5. customtriturated with diethyl ether (100 ml)
6. filtrationfiltered
7. customThe filtrate was evaporated under vacuum
8. customthe residue was chromatographed on silica gel (500 g)
9. washeluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph