Dimethylformamide → Ethyl alpha-fluoro-4-chlorophenylacetate

HRID 354702Notes

Reaction equation

HRID 354702 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F-:15].[K+].CN(C)C=O>O>[F:15][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 228840Ethyl 2-bromo-2-(4-chlorophenyl)acetateHCID 522689Potassium Fluoride

Product 1

HCID 13194587Ethyl alpha-fluoro-4-chlorophenylacetateYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl α-bromo-4-chlorophenylacetate (37.3 g), anhydrous potassium fluoride (9.7 g) and dry dimethylformamide (75 ml) was heated with stirring at a temperature of 140°-150° C. for a period of 6 hours. The reaction mixture was poured into water and the aqueous mixture extracted with methylene dichloride. The organic extract was washed with aqueous sodium carbonate, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The product was distilled using a spinning band column to give ethyl α-fluoro-4-chlorophenylacetate (7.5 g; 29%) b.p. 67° C. at 0.06 mm Hg.

Workup

  1. temperaturewas heated
  2. extractionthe aqueous mixture extracted with methylene dichloride
  3. extractionThe organic extract
  4. washwas washed with aqueous sodium carbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. distillationThe product was distilled

Sources & evidence

ORD record
ord-c966da82019f4dbca68a8f2821e9fd61
Source dataset
uspto-grants-1983_03
Patent number
US04376784

Reaction notes

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