Réaction #57520

Équation de réaction

(6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone

2,2′-azobisisobutyronitrile

N-bromosuccinimide

→

desired product

Rendement 68.5%

(6-Bromo-3-bromomethyl-benzofuran-2-yl)-(2,4-dichlorophenyl)-methanone

Rendement 68.5%

Solvants

carbon tetrachloride

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   Températureat reflux for 6 h
3. 3
   Autrethe resulting precipitate was removed by filtration
4. 4
   Concentrationthe filtrate was concentrated
5. 5
   AutreThe crude residue was purified by column chromatography (10% ethyl acetate in hexanes)

Mode opératoire

To a stirred solution of (6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (4.0 g, 10.4 mmol) in carbon tetrachloride (40 mL) was added 2,2′-azobisisobutyronitrile (AIBN) (171 mg, 1.04 mmol) and N-bromosuccinimide (1.95 g, 10.9 mmol). The reaction mixture was heated at reflux for 6 h, and upon cooling to rt, the resulting precipitate was removed by filtration and the filtrate was concentrated. The crude residue was purified by column chromatography (10% ethyl acetate in hexanes) to afford the desired product (3.30 g, 65% yield) as a white solid. Rf=0.68 (10% EtOAc in hexanes). 1H-NMR (acetone): δ 7.98(d, 1H), 7.91 (s, 1H), 7.74 (m, 2H), 7.64 (td, 2H), 5.16 (s, 2H).

Source