Hydrochloric Acid → 4-Fluoro-2-methyl-5-nitrophenyl 1-methylethyl ether

Participants

Reaction Steps

A solution of 4-fluoro-2-methyl-5-nitrophenol (D16) (0.85 mmol, 145 mg) in tetrahydrofuran (5 mL) was treated with 2-propanol (0.85 mmol, 51.1 mg, 1 eq), diphenyl-2-pyridylphosphine (1.28 mmol, 335.7 mg, 1.5 eq) and di-tert-butyl azodicarboxylate (1.28 mmol, 293.5 mg, 1.5 eq) under argon at room temperature. The mixture was stirred for 3 h then a solution of hydrogen chloride in ether (1M) was added and the mixture was stirred for 1 h. A gummy precipitate appeared. The mixture was concentrated under reduced pressure and the residue was dissolved in ether, washed twice with 5M aqueous hydrogen chloride solution for 30 min then washed twice with 10% aqueous sodium carbonate solution. The organic (ether) phase was dried and concentrated under reduced pressure to give a residue which was purified by chromatography on silica (ethyl acetate/petrol ether) to give the title compound as a pale yellow solid (0.53 mmol, 115 mg, 63% yield).

Provenance & Evidence