Thionyl Chloride → HCID 19835003, compound

HRID 477789Notes

Reaction equation

HRID 477789 reaction equation
[F:1][C:2]1[C:3]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:19][C:15]1[CH:16]=[CH:17][C:18]2[C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=3[CH2:11][O:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14626275HCID 14626275, compound

Product 1

HCID 19835003HCID 19835003, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7 g of 3-fluoro-2-[(3-fluorophenyloxy)methyl]benzoic acid and 50 g of thionyl chloride is refluxed with heating for 1 hour. After cooling to room temperature, dry toluene is added and the solvent is distilled off under reduced pressure. The residue is added with dichloromethane and the mixture is cooled to 0° C. Thereto 6 g of powdery anhydrous aluminum chloride is added and the mixture is stirred for 15 minutes and then added with ice-water, followed by extraction with toluene. After drying the extract 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 4.0 g of 3,7-difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 246(M+).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating for 1 hour
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionThe residue is added with dichloromethane
  5. temperaturethe mixture is cooled to 0° C
  6. additionThereto 6 g of powdery anhydrous aluminum chloride is added
  7. additionadded with ice-water
  8. extractionfollowed by extraction with toluene
  9. customAfter drying the
  10. extractionextract over magnesium sulfate
  11. distillationthe solvent is distilled off under reduced pressure
  12. washeluted with toluene

Sources & evidence

ORD record
ord-60e6ff339a9743edbfc76196729c61df
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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