1,2-Dibromoethane → 1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

Participants

Reaction Steps

A mixture of the potassium salt of 2-methoxy-4-nitrophenol (2.07 g, 10.0 mmol), 1,2-dibromoethane (1.72 mL, 20.0 mol), 1 N KOH (50 mL), tetrabutyl ammonium bromide (3.22 g 10.0 mol), and CH2Cl2 was stirred overnight. The reaction was diluted with 300 mL of EtOAc, washed with sat. NH4Cl solution (2×50 mL). The organic layer was dried over Na2SO4 prior to concentration in vacuum to a yellow solid. The solid was then washed with MeOH (2×5 mL) to yield 2.0 g (72%) of the title compound as a white solid. MS (ESI) 276, 278 (M+H)+.

Provenance & Evidence