Ethyl Acetate → 2-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

The mixture of 3-bromomethyl-7-nitro-3H-isobenzofuran-1-one (0.50 g, 1.84 mmol, Step E) and 4-tert-butylaniline (1.20 mL, 7.36 mmol) in 20 mL of THF was slowly warmed to RT from 0° C., then heated to reflux for 24 h. After cooling to RT, the mixture was diluted with H2O, and extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, condensed, and the titled compound was obtained as a light yellowish solid after column chromatography (10 to 35% of EtOAc in hexanes).

Provenance & Evidence