tert-Butanol → (2-Bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphorylazide (453 μL, 2.1 mmol) was added to a stirred solution of 2-bromo-3-methyl-5-nitro-benzoic acid ((Example 295: step e) 520 mg, 2 mmol) and triethylamine (1.4 mL, 2.1 mmol) in tert-butanol (25 mL) at rt. After 15 minutes, the reaction was heated to 80° C. for 16 h. EtOAc (100 mL) was added and the solution was extracted with solutions of citric acid (3×30 mL), NaHCO3, (2×30 mL) and brine (50 mL). Purification by column chromatography yielded the title compound as a white solid. 1H NMR (CDCl3) δ 8.93 (d, 1H, J=2.6 Hz), 7.77 (app dd, 1H, J=0.7, 2.8 Hz), 7.26 (br s, 1H), 2.51 (s, 3H), 1.55 (s, 9H).

Provenance & Evidence