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Methanol → 4-(4'-Chlorobenzenesulphonyl)biphenyl

HRID 16031
Notes
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Reaction equation

HRID 16031 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.CO>ClC1C(Cl)=C(Cl)C=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([C:4]2[CH:5]=[CH:6][C:1]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:2][CH:3]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 7095BiphenylHCID 73984-Chlorobenzenesulfonyl chloride

Product 1

HCID 6300224-(4'-Chlorobenzenesulphonyl)biphenylYield 65%

Reagents, catalysts & solvents 1

HCID 68951,2,3-TrichlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of biphenyl (10 g, 0.065 mol) and 4-chlorobenzenesulphonyl chloride (13.69 g, 0.065 mol) in trichlorobenzene (3 mL) was heated with stirring to 110° C. Anhydrous ferric chloride (0.05 g, 0.0003 mmol) was added and stirring was continued at 150° C. for 16 h. The cooled solid was stirred with methanol (200 mL). The product was filtered, washed with methanol, dried, and recrystallised from acetic acid to give 4-(4′-chlorobenzenesulphonyl)biphenyl (13.9 g, 65%); m.p. 169° C. (lit. 171-173° C.).

Workup

  1. temperaturewas heated
  2. stirringstirring
  3. filtrationThe product was filtered
  4. washwashed with methanol
  5. customdried
  6. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-75e276f8a4ae412098a9bb92b19f2df9
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07736539B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes