Water → 4-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

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Reaction Steps

In the case of compound 11, the required intermediate for step a) was synthesised as follows: To a stirred solution of 4-bromo-1-methyl-2-trifluoromethylbenzene (10 g) in tetrachloromethane (100 ml) at room temperature is added N-bromosuccinimide (7.5 g) and azobisisobutyronitrile (700 mg). After 15 h of stirring at reflux, the reaction is allowed to cool to room temperature, water is added and the reaction mixture is extracted twice with ethyl acetate. The organic layer is washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (9:1 cyclohexane:ethyl acetate) to yield 4-bromo-1-bromomethyl-2-trifluoromethylbenzene (7.1 g).

Provenance & Evidence