Pivaloyl chloride → HCID 3702406, compound

Participants

Reaction Steps

4-Fluoro-3-nitroaniline (500 mg, 3.20 mmol) and DMAP (586 mg, 4.80 mmol) were dissolved in 25 mL of DCM. Trimethylacetyl chloride (0.587 mL, 4.80 mmol) was added dropwise and the solution was stirred at rt for 3 h. The solution was washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 35% EtOAc in hexanes as eluent on silica gel to produce the desired title compound. Yield: 713 mg (93%). 1H NMR (400 MHz, CHLOROFORM-D:) δ 1.34 (s, 9H), 7.25 (dd, J=10.25, 9.08 Hz, 1H), 7.50 (br.s, 1H), 7.88 (ddd, J=9.08, 3.71, 2.83 Hz, 1H), 8.26 (dd, J=6.44, 2.73 Hz, 1H).

Provenance & Evidence