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Benzoyl Peroxide → alpha-Bromo-2-chloro-m-tolyl 2-thienyl ketone

HRID 461747
Notes
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Reaction equation

HRID 461747 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[C:9]([Cl:15])=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)=[O:7].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[C:9]([Cl:15])=[C:10]([CH2:14][Br:16])[CH:11]=[CH:12][CH:13]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 20211459HCID 20211459, compound

Product 1

HCID 21391797alpha-Bromo-2-chloro-m-tolyl 2-thienyl ketone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 11.8 parts of 2-chloro-m-tolyl 2-thienyl ketone, 8.9 parts of N-bromosuccinimide, 100 parts of carbon tetrachloride and 0.25 parts of benzoyl peroxide is stirred and refluxed for 2 hours. The precipitated succinimide is filtered off and washed on the filter with carbon tetrachloride. The filtrate is dried and evaporated, yielding α-bromo-2-chloro-m-tolyl 2-thienyl ketone as a residue.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe precipitated succinimide is filtered off
  3. washwashed on the
  4. filtrationfilter with carbon tetrachloride
  5. customThe filtrate is dried
  6. customevaporated

Sources & evidence

ORD record
ord-5bb4374b95d04416ae0188d68334a763
Source dataset
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04064132

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes