Sodium chlorodifluoroacetate → HCID 68153411, compound

HRID 1946921Notes

Reaction equation

HRID 1946921 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1.Cl[C:18]([F:23])([F:22])C([O-])=O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:18]([F:23])[F:22])=[N:14][CH:15]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2734985Sodium chlorodifluoroacetateHCID 68153395HCID 68153395, compound

Product 1

HCID 68153411HCID 68153411, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The 5-[1-(3-bromo-phenyl)-vinyl]-1H-pyridin-2-one (10 g, 1 eq) was dissolved in acetonitrile (180 ml) and degassed for 1 hour. Then sodium chlorodifluoroacetate (8.5 g, 1.2 eq) was added and the mixture heated to 100° C. overnight under a nitrogen atmosphere. The mixture was cooled to room temperature, the solvent was removed, and the crude was partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, dried over sodium sulphate, and concentrated in vacuo. The crude product was purified by flash chromatography eluting with ethyl acetate. The 5-[1-(3-bromo-phenyl)-vinyl]-2-difluoromethoxy-pyridine was obtained as colorless oil (2.6 g, 26% of theory). MS (ISP): m/z=328 [M+H]+.

Workup

  1. customdegassed for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was removed
  4. customthe crude was partitioned between water (100 ml) and ethyl acetate (100 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0f026bc43edd4a62b8a53b230c54aad8
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

Loading…