Potassium Carbonate → 2-(3,4,4-Trifluoro-3-butenylthio)oxazole

HRID 351792Notes

Reaction equation

HRID 351792 reaction equation
Br[CH2:2][CH2:3][C:4]([F:8])=[C:5]([F:7])[F:6].C(=O)([O-])[O-].[K+].[K+].[SH:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1>C(#N)C>[F:8][C:4](=[C:5]([F:7])[F:6])[CH2:3][CH2:2][S:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527879HCID 178527879, compound

Product 1

HCID 129939582-(3,4,4-Trifluoro-3-butenylthio)oxazoleYield 82.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.5 g of 4-bromo-1,1,2-trifluoro-1-butene and 7.0 g of potassium carbonate were added to 50 ml of acetonitrile, 3.8 g of 2-mercaptooxazole, and refluxed for 5 hours by heating. After cooling the reaction mixture to room temperature, solid substance was filtered by suction and the filtrate was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: hexane:dichloromethane=1:1) to obtain 6.5 g of 2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 82.7%, n20D=1.4631).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureby heating
  3. filtrationsolid substance was filtered by suction
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography (eluent: hexane:dichloromethane=1:1)

Sources & evidence

ORD record
ord-f0e2280a6d034b7d9edb609add3cb803
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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