Ethyl bromodifluoroacetate → HCID 66609731, compound

HRID 473129Notes

Reaction equation

HRID 473129 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.Br[C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>[Cu].CS(C)=O>[F:16][C:10]([F:17])([C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 69585Ethyl bromodifluoroacetateHCID 263440482-Bromo-5-fluoropyrimidine

Product 1

HCID 66609731HCID 66609731, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To 2-bromo-5-fluoropyrimidine (500 mg, 2.8 mmol) were added DMSO (1.5 mL), ethyl 2-bromo-2,2-difluoroacetate (0.4 mL, 3.1 mmol), and copper powder (390 mg, 6.16 mmol). The reaction vessel was sealed, and then evacuated and flushed with argon (2×). The mixture was heated at 50° C. overnight, then diluted with EtOH and filtered through Celite washing with EtOAc. To the filtrate was added water and the mixture was filtered through Celite again. The separated organic layer was washed with brine (2×), dried over sodium sulfate, and concentrated to afford ethyl 2,2-difluoro-2-(5-fluoropyrimidin-2-yl)acetate as an oil (470 mg, 76%). 1H NMR (300 MHz, CDCl3) δ 8.74 (s, 2H), 4.41 (q, J=7.2 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H).

Workup

  1. customThe reaction vessel was sealed
  2. customevacuated
  3. customflushed with argon (2×)
  4. additiondiluted with EtOH
  5. filtrationfiltered through Celite
  6. washwashing with EtOAc
  7. additionTo the filtrate was added water
  8. filtrationthe mixture was filtered through Celite again
  9. washThe separated organic layer was washed with brine (2×)
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-356bb1def8cc4c7ba21affb3e3d40727
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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