Bromide ion → 2-Acetoxymethyl-5-chloro-4-nitrobenzonitrile

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Reaction Conditions

Reaction Steps

The above partially purified bromide was dissolved in DMF (300 mL) and cooled to 0° C. Sodium acetate (18.0 g, 0.22 mol) was added. The mixture was stirred at 60° C. for 30 min. After cooling, the mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed with H2O (2×), dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel and elution with hexanes:EtOAc (9:1) yielded a front fraction containing 5-chloro-4-nitro-2-methylbenzonitrile and dibromide. Further elution with hexanes:EtOAc (2:1) gave the title compound (19.5 g, 47%) as a pale yellow solid.

Provenance & Evidence