Allyl bromide → 1,1-Bis(trifluoromethanesulfonyl)-3-butene

HRID 2211197Notes

Reaction equation

HRID 2211197 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[Cl-].[Mg+2].[K+].[F:8][C:9]([F:22])([F:21])[S:10]([CH2:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])(=[O:12])=[O:11].[Cl-].[Cl-]>C1COCC1>[F:19][C:17]([F:20])([F:18])[S:14]([CH:13]([S:10]([C:9]([F:8])([F:21])[F:22])(=[O:11])=[O:12])[CH2:3][CH:2]=[CH2:1])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 86749078Bis[(trifluoromethyl)sulfonyl] methane potassium magnesium chloride

Product 1

HCID 193761101,1-Bis(trifluoromethanesulfonyl)-3-butene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Next, 4,4-bis[(trifluoromethyl)sulfonyl]-1-butene was prepared by adding 3 ml of allyl bromide to 31.3 millimoles of the bis[(trifluoromethyl)sulfonyl] methane potassium magnesium chloride in 35 ml of THF. The mixture was stirred at 70° C. under reflux for 8 hours. After removal of solvent by distillation under reduced pressure, 50 ml of 3N hydrochloric acid was added to the residue and the aqueous solution was extracted with ethyl ether. The ethyl ether solution was dried with anhydrous MgSO4. The ethyl ether was removed from the solution and the product was distilled at 0.02 torr.

Workup

  1. temperatureunder reflux for 8 hours
  2. customAfter removal of solvent
  3. distillationby distillation under reduced pressure, 50 ml of 3N hydrochloric acid
  4. additionwas added to the residue
  5. extractionthe aqueous solution was extracted with ethyl ether
  6. dry with materialThe ethyl ether solution was dried with anhydrous MgSO4
  7. customThe ethyl ether was removed from the solution
  8. distillationthe product was distilled at 0.02 torr

Sources & evidence

ORD record
ord-f9d445e781a5474593383f9d5006ad80
Source dataset
uspto-grants-1995_10
Patent number
US05463005

Reaction notes

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