Ethyl Acetate → HCID 11020343, compound

HRID 907624Notes

Reaction equation

HRID 907624 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](Br)([F:15])[F:14])[CH3:10].C(OCC)(=O)C>CN(C=O)C>[CH2:9]([O:11][C:12](=[O:17])[C:13]([F:15])([F:14])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 96054-FluoroiodobenzeneHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 11020343HCID 11020343, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Fluoro-4-iodobenzene (30 g, 135 mmol) and 2-bromo2,2-difluoroacetic acid ethyl ester (29 g, 142.9 mmol) were dissolved in DMF (100 ml) and Cu (21.5 g, 71.2 mmol) was added. The reaction mixture was heated at 90° C. for 18 h. Ethyl acetate (100 ml) was added and the reaction mixture was quenched with a solution of potassium dihydrogen phosphate (20 g) in water (200 ml). The resultant solution was stirred for 30 min, filtered and was washed with ethyl acetate. The organic layer was separated, washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give 2,2-difluoro-2-(4-fluorophenyl)acetic acid ethyl ester (26.5 g) as a yellow liquid.

Workup

  1. customthe reaction mixture was quenched with a solution of potassium dihydrogen phosphate (20 g) in water (200 ml)
  2. filtrationfiltered
  3. washwas washed with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c52f25377984433a8144ca56a9cb0e6c
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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