Thionyl Chloride → 3,9-Difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one

HRID 477792Notes

Reaction equation

HRID 477792 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:19][C:15]1[CH:16]=[CH:17][C:18]2[C:7](=[O:9])[C:6]3[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH2:11][O:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 146262795-Fluoro-[(3-fluorophenyloxy)methyl]benzoic acid

Product 1

HCID 146262803,9-Difluoro-6,11-dihydrodibenz[b,e]oxepin-11-oneYield 46.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 10 g of 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoic acid is added 50 g of thionyl chloride and the mixture is refluxed with heating for 1 hour. After cooling the reaction mixture to room temperature, dry toluene is added and the solvent is distilled off under reduced pressure. The residue is added with dichloromethane and cooled to 0° C. Thereto 10 g of powdery anhydrous aluminum chloride is added and the mixture is stirred for 15 minutes. The reaction mixture is added with ice-water and extracted with toluene. After the extract is dried over magnesium fulfate, the solvent is distilled off under reduced pressure and the residue is subjected to silica-gel chromatography, followed by elution with toluene to give 4.3 g of 3,9-difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 246(M+).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 1 hour
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionThe residue is added with dichloromethane
  5. temperaturecooled to 0° C
  6. additionThereto 10 g of powdery anhydrous aluminum chloride is added
  7. additionThe reaction mixture is added with ice-water
  8. extractionextracted with toluene
  9. dry with materialAfter the extract is dried over magnesium fulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. washfollowed by elution with toluene

Sources & evidence

ORD record
ord-099f5cb335e14aeeb57fa5209be86c97
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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