反应详情

温度

130 °C

A mixture of 5-chloro-4-nitro-2-methylbenzonitrile (32.0 g, 0.16 mol), NBS (54.0 g, 0.30 mol) and benzoyl peroxide (200 mg, catalytic amount) in chlorobenzene was heated at 130° C. and irradiated with a sunlamp for 15 h. More NBS (30.0 g, 0.17 mol) and benzoyl peroxide (200 mg) were added. The mixture was further reacted for 24 h. After cooling, the precipitate formed was filtered off and washed with CH2Cl2. The combined filtrates were washed with H2O (2×), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was then chromatographed over silica gel and eluted with hexanes:EtOAc (9:1) to give 2-bromomethyl-5-chloro-4-nitrobenzonitrile (48 g, contaminated with starting material and dibrominated product) as a pale yellow solid.

1. customirradiated with a sunlamp for 15 h
2. customThe mixture was further reacted for 24 h
3. temperatureAfter cooling
4. customthe precipitate formed
5. filtrationwas filtered off
6. washwashed with CH2Cl2
7. washThe combined filtrates were washed with H2O (2×)
8. dry with materialdried over anhydrous MgSO4
9. concentrationconcentrated in vacuo
10. customThe residue was then chromatographed over silica gel
11. washeluted with hexanes:EtOAc (9:1)