Thionyl Chloride → HCID 14626282, compound

HRID 477793Notes

Reaction equation

HRID 477793 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:3]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][CH2:11][C:4]3[CH:3]=[C:2]([F:1])[CH:10]=[CH:9][C:5]=3[C:6](=[O:8])[C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14626281HCID 14626281, compound

Product 1

HCID 14626282HCID 14626282, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 15 g of 4-fluoro-2-[(4-fluorophenyoxy)methyl]benzoic acid is added 60 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 the mixture is cooled to 0° C. and added with 15 g of powdery anhydrous aluminum chloride, which is stirred for 15 minutes. The reaction mixture is added with ice-water and extracted with toluene. After the extract is successively 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 9.1 g of 2,8-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. temperaturethe mixture is cooled to 0° C.
  6. additionadded with 15 g of powdery anhydrous aluminum chloride, which
  7. additionThe reaction mixture is added with ice-water
  8. extractionextracted with toluene
  9. washAfter the extract is successively washed with water
  10. dry with materiala saturated saline solution and dried over magnesium sulfate
  11. distillationthe solvent is distilled off under reduced pressure
  12. washeluted with toluene

Sources & evidence

ORD record
ord-f133ec0c03014372bb360ffe01693f83
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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