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4-Toluenesulfonyl chloride → 1-Chloro-4-(4-methylbenzene-1-sulfonyl)benzene

HRID 2391
Notes
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Reaction equation

HRID 2391 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>O>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2862191-Chloro-4-(4-methylbenzene-1-sulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To 150 ml of chlorobenzene, 100.1 g (0.75 mol) of aluminum chloride was added, and further 143 g (0.75 mol) of p-toluenesulfonyl chloride was added dropwise over 1 hour. After stirred for 3 hours at 55° C., the reaction mixture was poured into 1.5 liter of water, and then the obtained crystal was filtered off and washed with n-hexane to obtain 140 g of the intended 4-methyl-4'-chlorodiphenylsulfone. NMR (heavy chloroform): δ7.9-7.8 (m, 4H), 7.5 (m, 2H), 7.3 (d, 2H), 2.4 (s, 3H).

Workup

  1. filtrationthe obtained crystal was filtered off
  2. washwashed with n-hexane

Sources & evidence

ORD record
ord-f69d3edd52d44422a14f922f370dc48b
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728879

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes