4-Toluenesulfonyl chloride → 2,2,3,3,4,4,4-Heptafluorobutyl 4-methylbenzene-1-sulfonate

HRID 1709087Notes

Reaction equation

ClC(Cl)C(F)(F)C(F)(F)C(F)(F)F.[F:14][C:15]([F:25])([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[CH2:16][OH:17].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[F:14][C:15]([F:25])([C:18]([F:23])([F:24])[C:19]([F:20])([F:21])[F:22])[CH2:16][O:17][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33]

Participants

Reactant 3

HCID 73974-Toluenesulfonyl chloride

HCID 9776Heptafluorobutanol

HCID 53813951HCID 53813951, compound

Product 1

HCID 20633992,2,3,3,4,4,4-Heptafluorobutyl 4-methylbenzene-1-sulfonate

Procedure

For example, to prepare 1,1-dichloro-2,2,3,3,4,4,4-heptafluorobutane, 2,2,3,3,4,4,4-heptafluorobutanol and p-toluenesulfonyl chloride are reacted to form 2,2,3,3,4,4,4-heptafluorobutyl-p-toluenesulfonate. Then, N-methylpyrrolidone, lithium chloride, and the 2,2,3,3,4,4,4-heptafluorobutyl-p-toluenesulfonate are reacted to form 1-chloro-2,2,3,3,4,4,4-heptafluorobutane. Finally, chlorine and the 1-chloro-2,2,3,3,4,4,4-heptafluorobutane are reacted to form the 1,1-dichloro-2,2,3,3,4,4,4-heptafluorobutane.

Workup

customare reacted

Sources & evidence

ORD record: ord-dbf63980ac3743e9ab4ccf60cdb659da
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04947881

Reaction notes

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