1,1-Dichloroethane → Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

HRID 1491574Notes

Reaction equation

HRID 1491574 reaction equation
[C:1]1([S:7][C:8]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.Cl[CH:26](Cl)C>CN(C)C=O>[C:1]1([S:7][C:8]2[CH:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH3:26])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 189779402-Phenylsulphenyl-4-trifluoromethylbenzoic acid

Product 1

HCID 18977929Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-phenylsulphenyl-4-trifluoromethylbenzoic acid (11.5 g), thionyl chloride (1 1.4 g), dimethylformamide (0.2 ml) and dichloroethane was heated at reflux for 90 minutes. The solution was then concentrated under reduced pressure and the residue was dissolved in methanol and heated at reflux for one hour. The resulting solution was poured into aqueous sodium bicarbonate and extracted with ether. The organic phase was dried over anhydrous sodium sulphate, filtered and evaporated. The resulting material was crystallised from hexane to give methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate (10.5 g) as white crystals, m.p. 58° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes
  3. concentrationThe solution was then concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol
  5. temperatureheated
  6. temperatureat reflux for one hour
  7. additionThe resulting solution was poured into aqueous sodium bicarbonate
  8. extractionextracted with ether
  9. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customThe resulting material was crystallised from hexane

Sources & evidence

ORD record
ord-c54025b16cc94423b4e1797ac98aaa3c
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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