2,3-Dichloropropene → HCID 90384249, compound

HRID 928677Notes

Reaction equation

HRID 928677 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[SH:10].Cl[C:12]([CH2:14]Cl)=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:3]2[S:10][C:12]([CH3:14])=[CH:13][C:4]=2[C:5]([F:9])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 50999469HCID 50999469, compound

Product 1

HCID 90384249HCID 90384249, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-4,5-difluorothiophenol (4.68 g, 20.8 mmol), 2,3-dichloro-1-propene (2.1 mL, 22.9 mmol), potassium carbonate (3.45 g, 24.9 mmol), and acetone (100 mL) were added, and stirred at 60° C. for 2 hours. The solvent was distilled away under reduced pressure, and after diluted with ethyl acetate, the resultant was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away, and to the resulting residue, dimethylaniline (50 mL) was added, and stirred at 220° C. overnight. After cooling, ethyl acetate and a 2 N hydrochloric acid aqueous solution were added to the reaction solution and stirred. After the insoluble material was filtered off, extraction was performed with ethyl acetate. The organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane) to thus obtain the title compound.

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. additionafter diluted with ethyl acetate
  3. washthe resultant was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away
  6. additionto the resulting residue, dimethylaniline (50 mL) was added
  7. stirringstirred at 220° C. overnight
  8. temperatureAfter cooling
  9. additionethyl acetate and a 2 N hydrochloric acid aqueous solution were added to the reaction solution
  10. stirringstirred
  11. filtrationAfter the insoluble material was filtered off
  12. extractionextraction
  13. washThe organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. distillationThe solvent was distilled away under reduced pressure
  16. customThe resulting residue was purified by silica gel chromatography (hexane)

Sources & evidence

ORD record
ord-9896ef128abd4c309f89dbb38819bb55
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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