Isopropanol → 1-Chloro-4-fluoro-5-nitro-2-(propan-2-yloxy)benzene

Participants

Reaction Steps

A mixture of 2-chloro-5-fluoro-4-nitrophenol (287 mg, 1.5 mmol), propan-2-ol (90 mg, 1.5 mmol), diphenyl-2-pyridylphosphine (592 mg, 2.25 mmol) and di-tert-butyl azodicarboxylate (518 mg, 2.25 mmol) in tetrahydrofuran (10 ml) was stirred at room temperature under argon for 22 hrs. The mixture was treated with 1M HCl/diethyl ether (10 ml) and stirred at room temperature for 1 hr, then concentrated under vacuum and the residue dissolved in diethyl ether (10 ml), treated with 5M HCl acid (10 ml) and stirred for 30 mins. The organic layer was separated, washed with 5M HCl acid (10 ml), then 10% Na2CO3 solution (2×10 ml), dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with 5-70% ethyl acetate/60-80 petrol ether to afford the title compound as a yellow solid (153 mg, 43%).

Provenance & Evidence