Isopropanol → 2-Fluoro-4-isopropoxy-1-nitrobenzene

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A mixture of 5-fluoro-4-nitrophenol (314 mg, 2.0 mmol), propan-2-ol (120 mg, 2.0 mmol), diphenyl-2-pyridylphosphine (789 mg, 3.0 mmol) and di-tert-butyl azodicarboxylate (691 mg, 3.0 mmol) in tetrahydrofuran (15 ml) was stirred at room temperature under argon for 22 hrs. The mixture was treated with 1M HCl/diethyl ether (15 ml) and stirred at room temperature for 2 hrs, then concentrated under vacuum and the residue dissolved in diethyl ether (10 ml), treated with 5M HCl acid and stirred for 2 hrs. The organic layer was separated, washed with 5M HCl acid (15 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 oil (276 mg, 69%).

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