Potassium Carbonate → 4-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

HRID 371015

Reaction equation

HRID 371015 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Br[CH:21]([CH3:31])[C:22]([O:29][CH3:30])=[CH:23][C:24]([O:26]CC)=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:21]([CH3:31])[C:22]([O:29][CH3:30])=[CH:23][C:24]([OH:26])=[O:25])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129406134-[2-Chloro-4-(trifluoromethyl)phenoxy]phenolHCID 53787831Ethyl 4-bromo-3-methoxypent-2-enoate

Product 1

HCID 538603484-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-chloro-4-trifluoromethylphenoxy)phenol (1.16 g), ethyl 4-bromo-3-methoxy-2-pentenoate (1.74 g) and potassium carbonate (0.73 g) in DMF (5 ml.) is heated to about 130° for 2 hours. Thereafter, DMF is removed. The residue is filtered and washed with methylene dichloride. The filtrate is washed, dried and evaporated to dryness. The oily residue is subjected to prep. thin layer chromatography using 20% ethylacetate/hexane to yield the ethyl ester of 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid, MS m/e 444 (M+).

Workup

  1. temperatureis heated to about 130° for 2 hours
  2. customThereafter, DMF is removed
  3. filtrationThe residue is filtered
  4. washwashed with methylene dichloride
  5. washThe filtrate is washed
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9c02d4b618d94bf1a8aa6cc5d9375c9d
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Linked notes

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