Boron trifluoride etherate → 6-Chloro-5-methylpyridin-3-ol

Participants

Reaction Steps

To a solution of boron trifluoride diethyl etherate (5.8 mL, 47.5 nmmol) in DME (18 mL) at -14° C. was added dropwise a solution of 5-amino-2-chloro-3-methylpyridine (4.5 g, 31.7 mmol) in DME (60 mL). The mixture was stirred for 15 minutes and then a solution of t-butyl nitrite (4.5 mL, 38 mmol) in DME (60 mL) was added dropwise. The mixture was stirred for 1 hour at 0° C., then pentane (100 mL) was added to give a solid. The solid was collected by filtration and dried to give the title compound (6.9 g): 1H NMR (MeOH-d4, 300 MHz) δ 2.58 (s, 3H), 8.86 (d, J=2.1 Hz, 1H), 9.41 (d, J=2.4 Hz, 1H).

Provenance & Evidence