Benzoyl Peroxide → Methyl 5-(bromomethyl)thiophene-2-carboxylate

HRID 963505Notes

Reaction equation

HRID 963505 reaction equation
[CH3:1][O:2][CH:3]([O:10]C)[C:4]1[S:5][C:6]([CH3:9])=[CH:7][CH:8]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[S:5][C:6]([CH2:9][Br:12])=[CH:7][CH:8]=1)=[O:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19081167HCID 19081167, compound

Product 1

HCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 2-dimethoxymethyl-5-methylthiophene (3.44 g, 20 mmol) and N-bromosuccinimide (4.63 g, 26 mmol) in carbon tetrachloride (50 ml) was added a catalytic amount of benzoylperoxide. The mixture was refluxed for 1 hour. Undissolved materials were filtered off. The filtrate and the washings were combined and evaporated in vacuo to give 2-methoxycarbonyl-5-bromomethyl-thiophene as a yellow oil (4.65 g}, which was used in a following reaction without further purification.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. filtrationUndissolved materials were filtered off
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-1c77bb77552b430c9e8e5c6f1b0aec32
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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