2-Tert-Butylphenol → Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-3-nitropyridine (21.05 g, 132.7 mmol) in DMF (100 mL) was treated with 2-tert-butylphenol (23.5 mL, 152.6 mmol) and cesium carbonate (129.8 g, 398.3 mmol). The mixture was heated at 80° C. for 30 h. The reaction was cooled to rt, and the mixture was poured in water (1 L) with stirring. The yellow precipitate formed was filtered and washed with water, and recrystallized from ethanol to afford 1a as beige crystals (32.83 g, 90%). 1H NMR (400 MHz, CD3OD) δ ppm 1.34 (s, 9H), 6.93 (m, 1H), 7.22 (m, 3H), 7.47 (m, 1H), 8.31 (dd, J=4.82, 1.75 Hz, 1H), 8.46 (dd, J=7.89, 1.75 Hz, 1H).

Provenance & Evidence