Perchloric Acid → tert-Butyl 2,6-dichloro-4,5-dimethylnicotinate

Participants

Reaction Steps

To a solution of 2,6-dichloro-4,5-dimethylnicotinic acid (2.75 g, 12.5 mmol, 1 equiv) in tertbutyl acetate (83 mL) was added concentrated perchloric acid (3.2 mL, 37.5 mmol, 3 equiv). The reaction was stirred 1 h and then diluted with EtOAc. The organic solution was then washed with 10% potassium carbonate, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by silica gel flash column chromatography (0-100% DCM/hexane) to provide the product (2.50 g, 72%) as a waxy white solid. 1H NMR (400 MHz, CDCl3) δ 2.35 (s, 3H), 2.32 (s, 3H), 1.62 (s, 9H); LCMS (ESI, M+1): 276.00.

Provenance & Evidence