1-Chloro-4-nitrobenzene → HCID 70123326, compound

Participants

Reaction Steps

108.9 mg of potassium t-butoxide and 134.1 mg of 4-chloronitrobenzene were added to a solution of 156.6 mg of 2-(1-hydroxy-1-methylethyl)benzothiazole [prepared as described in step (a) above] in 3.1 ml of dimethylformamide at room temperature. The resulting mixture was stirred at room temperature for 3 hours, and then it was stirred at 60° C. for a further 4 hours. The temperature of the reaction mixture was then raised to 90° C. and the mixture stirred at this temperature for a further 5 hours, after which it was cooled to room temperature. A saturated aqueous ammonium chloride solution was then added to the reaction mixture and the mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 197.1 mg (yield 70%) of the title compound as an oil.

Provenance & Evidence