m-Chloroperbenzoic acid → 2-(4,4'-Difluorobenzhydrylidene)-1,3,5-trithiane-5-oxide

HRID 1194773Notes

Reaction equation

HRID 1194773 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6](=[C:14]2[S:19][CH2:18][S:17][CH2:16][S:15]2)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[F:13][C:10]1[CH:9]=[CH:8][C:7]([C:6](=[C:14]2[S:15][CH2:16][S:17](=[O:30])[CH2:18][S:19]2)[C:5]2[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 143292842-(4,4'-Difluorobenzhydrylidene)-1,3,5-trithiane

Product 1

HCID 143293802-(4,4'-Difluorobenzhydrylidene)-1,3,5-trithiane-5-oxideYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 30 ml of dichloromethane of 1.5 g of 2-(4,4'-difluorobenzhydrylidene)-1,3,5-trithiane was added 0.77 g of m-chloroperbenzoic acid in small portions at 0° C., and the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was poured into ice-water and extracted with dichloromethane. Usual work up gave crude solid, which was purified by a silica gel column chromatography (chloroform:hexane=3:1) to obtain 1.2 g of white crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with dichloromethane
  3. customUsual work up gave crude solid, which
  4. customwas purified by a silica gel column chromatography (chloroform:hexane=3:1)

Sources & evidence

ORD record
ord-857ed7a4dcee4e3a9a317a7ac8fcb77c
Source dataset
uspto-grants-1989_03
Patent number
US04816475

Reaction notes

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