Water → 2-(Bromomethyl)-4-methoxy-1-nitrobenzene

Participants

Reaction Steps

The reaction apparatus consisted of a 50-mL single-necked round-bottom flask equipped with a water-jacketed condensor, magnetic stirrer, and an argon-filled balloon. A solution of 5-methoxy-2-nitrotoluene (0.25 g, 1.50 mmol), carbon tetrachloride (25 mL), a catalytic amount of benzoyl peroxide (25 mg, 0.83 mmol), and N-bromosuccinimide (0.32 g, 1.8 mmol) were added to the reaction flask. The mixture was refluxed and irradiated under a 90-watt lamp (GE watt-miser light bulb, 130 V, 1000 hrs) for 5 h and then cooled to room temperature. The precipitated succinimide was removed by gravity filtration and the filtrate was extracted with sodium metabisulfite (28 M, 1×50 mL) and water (1×50 mL). The organic layer was separated, dried over sodium sulfate, filtered and then evaporated to afford a crude oil (382 mg, 105%). The crude product was chromatographed on silica gel (hexane/EtOAc=9:1) to give the product as yellow crystals (172 mg, 47%): m.p. 64–65° C.

Provenance & Evidence