Water → HCID 14626274, compound

HRID 477787Notes

Reaction equation

HRID 477787 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[F:10][C:11]1[C:12]([CH2:22]Br)=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].O>C(O)C>[F:10][C:11]1[C:12]([CH2:22][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 97433-FluorophenolHCID 5360545SodiumHCID 14626273Ethyl 2-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 14626274HCID 14626274, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.3 g of sodium metal in 100 ml of ethanol are added 6.3 g of 3-fluorophenol and 13 g of ethyl 3-fluoro-2-bromomethylbenzoate and the mixture is refluxed with heating for 8 hours. After cooling, 300 ml of water is added and the mixture is extracted with toluene. After the extract is washed with water and a saturated saline solution and dried over magnesium sulfate, the solvent is distilled off under reduced pressure. The residue is subjected to silica-gel chromatography and eluted with toluene to give 13 g of ethyl 3-fluoro-2-[(3-fluorophenyl oxy)methyl]benzoate (oil). Mass spectrum m/z: 292(M+).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 8 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with toluene
  5. washAfter the extract is washed with water
  6. dry with materiala saturated saline solution and dried over magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. washeluted with toluene

Sources & evidence

ORD record
ord-f90bf39688424761bedb7c925ef97d34
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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