Ethylene Glycol → Ethyl alpha-fluoro-3-chloro-4-cyclohexylphenylacetate

HRID 436319Notes

Reaction equation

HRID 436319 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F-:21].[K+].C(O)CO>O>[F:21][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 522689Potassium FluorideHCID 21454151Ethyl alpha-bromo-3-chloro-4-cyclohexylphenylacetate

Product 1

HCID 21454173Ethyl alpha-fluoro-3-chloro-4-cyclohexylphenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 118 g. (0.33 moles) of ethyl α-bromo-3-chloro-4-cyclohexylphenylacetate is vigorously stirred at 130°-140° C with 29 g. (0.5 moles) of potassium fluoride in 100 ml. of ethylene glycol for 12 hours. The reaction mixture is cooled and 400 ml. of water is added and the crude product separates. The aqueous glycol mixture is extracted with ether, the ether is then dried, evaporated to dryness and upon distillation results in ethyl α-fluoro-3-chloro-4-cyclohexylphenylacetate.

Workup

  1. additionA mixture of 118 g
  2. temperatureThe reaction mixture is cooled
  3. extractionThe aqueous glycol mixture is extracted with ether
  4. dry with materialthe ether is then dried
  5. customevaporated to dryness and upon distillation
  6. customresults in ethyl α-fluoro-3-chloro-4-cyclohexylphenylacetate

Sources & evidence

ORD record
ord-113525ccedfe4fd684648d492b026aaf
Source dataset
uspto-grants-1977_02
Patent number
US04008269

Reaction notes

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