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

Temperature

50 °C

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).

1. filtrationfiltered through Celite
2. additionThen water and EtOAc were added
3. stirringthe mixture was shaken
4. filtrationagain filtered through Celite
5. washThe organic layer was washed with water (1×) and brine (1×)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-eb421416065e48c08a05f2a3fd780c04

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633207B2