Dimethyl Sulfoxide → HCID 12815947, compound

HRID 1388539Notes

Reaction equation

HRID 1388539 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([S:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[Cl:14].C([O-])(=[O:17])C.[K+].CS(C)=O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:14][C:4]1[CH:5]=[CH:6][C:7]([S:9][C:10]([F:13])([F:12])[F:11])=[CH:8][C:3]=1[CH2:2][OH:17]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 12815944HCID 12815944, compound

Product 1

HCID 12815947HCID 12815947, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 55.7 g of crude 2-chloromethyl-4-(trifluoromethylthio)chlorobenzene, 23 g of potassium acetate, 150 ml of dimethyl sulfoxide and 10 g of triethylbenzylammonium chloride is stirred for 5 hours at 60° C. It is decomposed by pouring into water, extracted with benzene and the benzene evaporated. The oily residue is dissolved in 200 ml of ethanol, 100 ml of water and 20 ml of hydrochloric acid are added and the mixture is stirred and refluxed for 7 hours. Ethanol is distilled off, the residue mixed with water and extracted with benzene. The oil obtained by evaporation of the dried extract, is distilled in vacuo. There are obtained 40.2 g crude 2-chloro-5-(trifluoromethylthio)benzyl alcohol boiling at 140°-150° C./2 kPa. According to the 1H-NMR spectrum the product contains approximately 80% of the named compound and the remainder is the position isomer. In this state the substance is suitable for further processing.

Workup

  1. extractionextracted with benzene
  2. customthe benzene evaporated
  3. dissolutionThe oily residue is dissolved in 200 ml of ethanol
  4. addition100 ml of water and 20 ml of hydrochloric acid are added
  5. stirringthe mixture is stirred
  6. temperaturerefluxed for 7 hours
  7. distillationEthanol is distilled off
  8. additionthe residue mixed with water
  9. extractionextracted with benzene
  10. customThe oil obtained by evaporation of the dried
  11. extractionextract
  12. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-850dc277fe464c80af6cdc1cd06e7244
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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