Dimethylformamide → 2,2-Difluoro-2-phenylacetyl chloride

HRID 1060210Notes

Reaction equation

HRID 1060210 reaction equation
[F:1][C:2]([F:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:16])=O.CN(C)C=O>C(Cl)Cl>[C:6]1([C:2]([C:3]([Cl:16])=[O:4])([F:12])[F:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7261532,2-Difluoro-2-phenylacetic acid

Product 1

HCID 224753152,2-Difluoro-2-phenylacetyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with 2,2-difluoro-2-phenylacetic acid (0.8 g, 5.06 mmol), as prepared in the preceding step, under argon in an ice-bath was added oxalyl chloride (5 mL), and the reaction mixture stirred for 15 min. A solution of dimethylformamide (DMF) (37 mg, 0.506 mmol) in DCM (0.5 mL) was added. After 2 hours, the ice-bath was removed, and the mixture continued to stir for 1 hour. The solvents were evaporated, DCM was added, and then evaporated in vacuo giving the title compound (0.88 g, 98% yield), that was used immediately without further purification.

Workup

  1. customas prepared in the preceding step, under argon in an ice-bath
  2. waitAfter 2 hours
  3. customthe ice-bath was removed
  4. stirringto stir for 1 hour
  5. customThe solvents were evaporated
  6. additionDCM was added
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-691f9e9e893f4b9884400426eb75463d
Source dataset
uspto-grants-2003_02
Patent number
US06521663B2

Reaction notes

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