Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

HRID 901944Notes

Reaction equation

HRID 901944 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:7][C:6]1[C:2]([Cl:1])=[C:3]([C:8]([O:10][CH3:11])=[O:9])[S:4][CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2777567Methyl 3-chloro-4-methylthiophene-2-carboxylate

Product 1

HCID 18376575Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylateYield 39%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 3-chloro-4-methylthiophenecarboxylate (10 g, 53 mmol), N-bromosuccinimide (9.4 g, 53 mmol) and azo-bis-(isobutyronitrile) (860 mg, 5.3 mmol) in carbon tetrachloride (300 ml) was heated at reflux for 18 h. The mixture was filtered and reduced. Chromatography (10% EtOAc/90% hexanes) afforded methyl 4-bromomethyl-3-chlorothiophene-2-carboxylate (5.5 g, 39%) as a white solid.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-c153adddf8964eab96439cd0dfd244d4
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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