Phosphorus oxychloride → 3-(Trifluoromethyl)phenylmethanesulfonyl chloride

HRID 476518Notes

Reaction equation

HRID 476518 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][S:7]([O-])(=[O:9])=[O:8].[Na+].P(Cl)(Cl)([Cl:19])=O>>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][S:7]([Cl:19])(=[O:9])=[O:8]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23700704Sodium 3-trifluoromethylbenzylsulfonate

Product 1

HCID 27946463-(Trifluoromethyl)phenylmethanesulfonyl chlorideYield 90.2%

Procedure

10 g of sodium 3-trifluoromethylbenzylsulfonate was slowly added to 17.7 ml (29.1 g) of phosphorous oxychloride. The resulting slurry was stirred at 100° to 105° C. for five hours. The reaction mixture was then cooled and filtered. The filter cake was washed with methylene chloride, the washings were combined with the filtrate and then evaporated to dryness affording 8.9 g of 3-trifluoromethylbenzylsulfonyl chloride.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with methylene chloride
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-51a77baf777e493a98ac7c412476fd90
Source dataset
uspto-grants-1989_12
Patent number
US04885027

Reaction notes

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