Acetonitrile → 4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester

HRID 4461Notes

Reaction equation

HRID 4461 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([F:16])[CH:3]=1.Br[CH:18]([CH3:27])[C:19]([O:25][CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:18]([CH3:27])[C:19]([O:25][CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:12]=2)=[C:4]([F:16])[CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 135337314-(4-Bromo-2-fluorophenoxy)phenolHCID 54279858Methyl 4-bromo-3-methoxypent-2-enoate

Product 1

HCID 867419984-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl esterYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.0 g (42.4 mmol) 4-(4-bromo-2-fluorophenoxy)phenol, 9.5 g (42.4 mmol) methyl 4-bromo-3-methoxy-2-pentenoate, 6.45 g (46.6 mmol) potassium carbonate and 180 ml acetonitrile was heated at reflux for 16 hours. The mixture was poured into water and extracted with ether. The combined ether extracts were washed with dilute aqueous NaOH, washed with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC eluting with 95:5 hexane:acetone, to give 10.5 g (58 percent) of the product as a clear colorless oil. Calc: C, 53.66; H, 4.27. Found: C, 53.28, H, 4.40. Structure was established on the basis of IR and NMR analysis.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. extractionextracted with ether
  4. washThe combined ether extracts were washed with dilute aqueous NaOH
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed by rotary evaporation
  8. customThe residue was purified by HPLC
  9. washeluting with 95:5 hexane

Sources & evidence

ORD record
ord-b5402a5a3ee14b03bfb946e023674692
Source dataset
uspto-grants-1988_02
Patent number
US04725683

Reaction notes

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