Water → (3,4-Difluoro-phenyl)acetic acid allyl ester

HRID 1172214Notes

Reaction equation

HRID 1172214 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21].O>CN(C)C=O>[CH2:21]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 69571(3,4-Difluorophenyl)acetic acid

Product 1

HCID 67422777(3,4-Difluoro-phenyl)acetic acid allyl esterYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3,4-Difluorophenyl)acetic acid (52 g; 0.3 mol) was dissolved in N,N-dimethylformamid (200 mL). Potassium carbonate (61 g, 0.45 mol) was added and the mixture was stirred at room temperature (rt) for 15 min. Allyl bromide (47 g, 0.39 mol) was added and the suspension was stirred at room temperature for 20 h. The mixture was thrown into water (250 mL) and extracted with diethylether (2×300 mL). The combined organic phases were washed with water (4×100 mL), dried (Magnesium sulphate) and evaporated in vacuo to give 64 g (3,4-Difluoro-phenyl)acetic acid allyl ester as a clear oil.

Workup

  1. stirringthe suspension was stirred at room temperature for 20 h
  2. extractionextracted with diethylether (2×300 mL)
  3. washThe combined organic phases were washed with water (4×100 mL)
  4. dry with materialdried (Magnesium sulphate)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-473c32ea026a45ebb6776333d43842a3
Source dataset
uspto-grants-2010_11
Patent number
US07834008B2

Reaction notes

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