Potassium Carbonate → 2-(2-Ethylsulfanyl-4-trifluoromethylsulfanyl-phenyl)-5-trifluoromethylsulfanylbenzoxazole

HRID 1750064Notes

Reaction equation

HRID 1750064 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH:13]=1)=O.Br[C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=1[S:28][CH2:29][CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:29]([S:28][C:18]1[CH:19]=[C:20]([S:23][C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([S:3][C:2]([F:15])([F:14])[F:1])=[CH:13][C:9]=2[N:10]=1)[CH3:30]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 1180354975-((Trifluoromethyl)sulfinyl)benzo[d]oxazoleHCID 1180355631-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene

Product 1

HCID 1180353892-(2-Ethylsulfanyl-4-trifluoromethylsulfanyl-phenyl)-5-trifluoromethylsulfanylbenzoxazoleYield 15.5%

Reagents, catalysts & solvents 5

HCID 165397Cupric acetate monohydrateCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.10 g of 5-trifluoromethylsulfinylbenzoxazole, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was extracted with ethyl acetate and then dried with anhydrous sodium sulfate. The residue obtained by concentrating the mixture under reduced pressure was applied to a silica gel column chromatography to obtain 0.03 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanyl-phenyl)-5-trifluoromethylsulfanylbenzoxazole (hereinafter, referred to as Compound 19).

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. concentrationby concentrating the mixture under reduced pressure

Sources & evidence

ORD record
ord-17ceabe3a46947c0ab7d1dbbe3b97cd2
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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