2-Chloroethanol → 1-(2-chloroethoxy)-2-nitrobenzene

Participants

Reaction Steps

A mixture of ortho-nitrophenol (5.0 g, 35.8 mmoles) and 2-chloroethanol (9.5 ml, 143 mmoles) in THF (50 mL), in a round bottom flask, under nitrogen, was stirred at room temperature. Triphenylphosphine (14 g, 53.7 mmoles) was added, followed by diethylazodicarboxylate dropwise (8.5 mL, 53.7 mmoles). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, extracted with EtOAc, washed with water (1×), brine (1×), dried (Na2SO4), and concentrated under vacuum. The crude product was purified by flash chromatography using as eluent 40% EtOAc/hexane to give the title compound as an off-white solid (5.6 g, 28 mmoles).

Provenance & Evidence