m-Chloroperbenzoic acid → 2-(Perfluorooctylsulfinyl)biphenyl

HRID 974070Notes

Reaction equation

HRID 974070 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:49])([S:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21]>C(Cl)Cl>[F:49][C:13]([F:12])([S:36]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:9])[C:14]([F:34])([F:35])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 156553492-(Perfluorooctylthio)biphenyl

Product 1

HCID 156553482-(Perfluorooctylsulfinyl)biphenylYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, 3.57g (14.5 mmol) of m-chloroperbenzoic acid was added little by little to a solution of 8.76 g (14.5 mmol) of 2-(perfluorooctylthio)biphenyl in 50 ml of methylene chloride with stirring. The mixture was stirred overnight at room temperature. The precipitate in the reaction mixture was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexane as an eluent to give 8.97 g (100%) of 2-(perfluorooctylsulfinyl)biphenyl as while crystals. The properties of the product were as shown below.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe precipitate in the reaction mixture was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e839586108594d4d8e2d03a4b10d863d
Source dataset
uspto-grants-1991_11
Patent number
US05066795

Reaction notes

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