Benzoyl Peroxide → [4-(1-Bromoethyl)phenyl](thiophen-2-yl)methanone

HRID 258921Notes

Reaction equation

HRID 258921 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=1)=[O:7].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1(C)C=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[CH:9]=[CH:10][C:11]([CH:14]([Br:16])[CH3:15])=[CH:12][CH:13]=1)=[O:7]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1043214-Ethylphenyl 2-thienyl ketone

Product 1

HCID 103685[4-(1-Bromoethyl)phenyl](thiophen-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 1140TolueneCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 23.5 parts of p-ethylphenyl 2-thienyl ketone, 19.5 parts of N-bromosuccinimide, 220 parts of carbon tetrachloride, 1.1 parts of benzoyl peroxide and one drop of toluene is stirred and refluxed for 2 hours. The precipitated succinimide is filtered off and the carbon tetrachloride filtrate is dried and evaporated. The oily residue solidifies on cooling. The solid product is dissolved in 2-propanol and the product is allowed to crystallize. It is filtered off and dried in vacuo, yielding α-bromo-α-methyl-p-tolyl 2-thienyl ketone; mp. 71.1° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe precipitated succinimide is filtered off
  3. dry with materialthe carbon tetrachloride filtrate is dried
  4. customevaporated
  5. temperatureon cooling
  6. dissolutionThe solid product is dissolved in 2-propanol
  7. customto crystallize
  8. filtrationIt is filtered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-de0992edeaa14a218cdd4f2ab40b388b
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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