Benzyl Alcohol → Benzyl 6-chloropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sulfurous dichloride (6.8 g, 57 mmol) was added to a solution of 6-chloronicotinic acid (4.5 g, 28.5 mmol) in toluene (40 mL) at 0° C. The mixture was stirred at 110° C. for 2 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. Benzyl alcohol (4.65 g, 43.1 mmol), pyridine (6.9 mL) and toluene (50 mL) were added to the residue. The mixture was stirred at 25° C. for 3 hours. HCl (20 mL, 4 N) was added and the mixture was extracted with toluene. The toluene layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford benzyl 6-chloronicotinate. MS ESI calc'd. for C13H11ClNO2 [M+H]+ 248. found 248. 1HNMR (400 MHz, DMSO-d6) δ 8.94 (d, J=2.0 Hz, 1H), 8.34-8.31 (m, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.50-7.17 (m, 5H), 5.38 (s, 2H).

Provenance & Evidence