Ethyl bromodifluoroacetate → Ethyl 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-bromo-5-fluoropyridine (2 g, 11.36 mmol) and ethyl 2-bromo-2,2-difluoroacetate (1.6 mL, 12.5 mmol) in DMSO (4 mL) was added copper powder (1.6 g, 24.98 mmol) and the mixture was stirred at 50° C. overnight in a sealed flask. The mixture was diluted with DMSO (10 mL) and filtered through Celite. Then water and EtOAc were added and the mixture was shaken and again filtered through Celite. The organic layer was washed with water (1×) and brine (1×) and dried over sodium sulfate, and concentrated to afford ethyl 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate as a yellow oil (1.5 g, 60%). 1H NMR (300 MHz, CDCl3) δ 1.34 (t, 3H), 4.38 (q, 2H), 7.56 (dt, 1H), 7.77 (dd, 1H), 8.50 (d, 1H).

Provenance & Evidence