1,1-Bis(trifluoromethanesulfonyl)-3-butene → 4,4-Bis(trifluoromethanesulfonyl)butyldichloromethylsilane

HRID 631019Notes

Reaction equation

HRID 631019 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([CH:6]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[CH2:7][CH:8]=[CH2:9])(=[O:5])=[O:4].[Cl:19][CH:20]([SiH3:22])[Cl:21]>C1CC=CCCC=C1.Cl[Pt]Cl.C1(C)C=CC=CC=1>[F:14][C:13]([F:15])([F:16])[S:10]([CH:6]([S:3]([C:2]([F:17])([F:1])[F:18])(=[O:4])=[O:5])[CH2:7][CH2:8][CH2:9][SiH2:22][CH:20]([Cl:21])[Cl:19])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 193761101,1-Bis(trifluoromethanesulfonyl)-3-buteneHCID 57353436(Dichloromethyl)silane

Product 1

HCID 1234186174,4-Bis(trifluoromethanesulfonyl)butyldichloromethylsilaneYield 95.3%

Reagents, catalysts & solvents 2

HCID 5702648Platinum, dichloro((1,2,5,6-eta)-1,5-cyclooctadiene)-CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

Under nitrogen atmosphere, a three-neck flask equipped with a reflux condenser and having a volume of 100 ml was charged with each of 126.7 g (0.393 mol) of 1,1-bis(trifluoromethanesulfonyl)-3-butene, 68.7 g of toluene, 15.2 mg (0.0002 parts by mass relative to BTSB) of dichloro(1,5-cyclooctadiene)platinum(II) (made by Tokyo Chemical Industry Co., Ltd.), and 50.0 g (0.4 parts by mass relative to BTSB) of dichloromethylsilane (made by Tokyo Chemical Industry Co., Ltd.). Continuously, under nitrogen atmosphere, stirring was conducted for three minutes for mixing. After that, while this flask was heated by immersion in an oil bath adjusted to 50° C., an addition reaction was conducted for 30 minutes. After termination of the addition reaction, toluene was distilled out under reduced pressure and recovered. Then, a distillation under reduced pressure was conducted. Under a reduced pressure of 533 Pa (4 mmHg), it was distilled out by heating at 105-115° C., thereby obtaining 163.0 g of 4,4-bis(trifluoromethanesulfonyl)butyldichloromethylsilane (in the following, it may be abbreviated as BTSB-DCMS) as a perfluoromethidization agent.

Workup

  1. customUnder nitrogen atmosphere, a three-neck flask equipped with a reflux condenser
  2. additionfor mixing
  3. temperatureAfter that, while this flask was heated by immersion in an oil bath
  4. customadjusted to 50° C.
  5. additionan addition reaction
  6. waitwas conducted for 30 minutes
  7. distillationwas distilled out under reduced pressure
  8. customrecovered
  9. distillationThen, a distillation under reduced pressure
  10. distillationUnder a reduced pressure of 533 Pa (4 mmHg), it was distilled out

Sources & evidence

ORD record
ord-d05579ce33ee4a798ecaa533419ff371
Source dataset
uspto-grants-2016_04
Patent number
US09318764B2

Reaction notes

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