Acetic Acid → HCID 21904679, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-chloronicotinic acid (2.36 g, 10 mmol), 4-trifluoromethoxyphenol (2.14 g, 12 mmol) and K2CO3 (4.14 g, 30 mmol) in DMF (30 mL) was heated at 140° C. for 24 h. After cooling to room temperature the mixture was diluted with water (150 mL) and the pH was adjusted to 6 with acetic acid. The mixture was extracted with EtOAc (3×50 mL) and the combined organic extracts were dried (MgSO4) and evaporated to give an oil. This was triturated with water to give a sticky solid which was filtered and washed with water and then pentane. The resulting beige solid was suspended in further pentane, sonicated, filtered and dried in vacuo at 60° C. to give the product (0.92 g, 24%) as a beige solid; (δH (CDCl3, 300 MHz) 7.19 (2H, m), 7.28 (2H, m), 8.35 (1H, s), 8.58 (1H, s); MS m/z (TS+) 378, 380 (MH+).

Provenance & Evidence