Water → Ethyl 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoate

HRID 477790Notes

Reaction equation

HRID 477790 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[CH:12]=[CH:13][C:14]([CH2:22]Br)=[C:15]([CH:21]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].O>C(O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:22][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)=[C:15]([CH:21]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 97433-FluorophenolHCID 5360545SodiumHCID 14626277Ethyl 2-(bromomethyl)-5-fluorobenzoate

Product 1

HCID 14626278Ethyl 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoateYield 105.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.5 g of sodium metal in 100 ml of ethanol are added 8 g of 3-fluorophenol and 17 g of ethyl 5-fluoro-2-bromomethylbenzoate [U.S. Pat. No. 4,082,850]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. The extract is washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give 20 g of ethyl 5-fluoro-2-[(3-fluorophenyl oxy)methyl]benzoate (oil). Mass spectrum m/z: 292(M+).

Workup

  1. temperature4,082,850]and the mixture is refluxed
  2. temperaturewith heating for 8 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with toluene
  5. washThe 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

Sources & evidence

ORD record
ord-3efcb309c61045da9ed872907fc21c6c
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

Loading…