Lithium Hydroxide → 5-(Difluoromethoxy)picolinic acid

Participants

Reaction Steps

To a solution of methyl 5-(difluoromethoxy)picolinate from step K2 (730 mg, 3.59 mmol) in THF (8 mL), was added a solution of lithium hydroxide (430 mg, 18.0 mmol) in water (5 mL). The mixture was stirred at rt for 3 h, then concentrated in vacuo. After the addition of 10 mL of 1 N HCl, 150 mL of EtOAc was added. The resulting mixture was washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-(difluoromethoxy)picolinic acid (610 mg, 3.23 mmol, 90% yield). LCMS (M+H)+=190.1. 1H NMR (500 HMz, chloroform-d) δ 8.52 (d, J=2.0 Hz, 1H), 8.30 (d, J=8.5 Hz, 1H), 7.74 (dd, J=8.5, 2.6 Hz, 1H), 6.84-6.53 (m, 1H).

Provenance & Evidence