Reaktion #43927

Reaktionsgleichung

4-bromo-3,5-dimethylphenyl acetate

N-bromosuccinimide

→

title compound

Ausbeute 73.0%

4-bromo-3-(bromomethyl)-5-methylphenyl acetate

Ausbeute 73.0%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue was diluted with diethyl ether
4. 4
   Filtrationthe insoluble substance was filtered off
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe residue was-purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

Vorschrift

A suspension of 4-bromo-3,5-dimethylphenyl acetate (12.1 g, 49.8 mmol), N-bromosuccinimide (9.79 g, 55.0 mmol) and 2,2′-azobisisobutyronitrile (82.1 mg, 0.500 mmol) in carbon tetrachloride (100 mL) was stirred at 75° C. for 5 hr under nitrogen atmosphere. The reaction mixture was ice-cooled, and concentrated under reduced pressure. The residue was diluted with diethyl ether, the insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was-purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (11.7 g, yield 73%) as colorless crystals.

Quelle