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

HRID 643778

Reaction equation

HRID 643778 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][O:28][C:29]([C:31]1[S:32][C:33]([CH3:36])=[CH:34][CH:35]=1)=[O:30]>C(Cl)(Cl)Cl>[CH3:27][O:28][C:29]([C:31]1[S:32][C:33]([CH2:36][Br:1])=[CH:34][CH:35]=1)=[O:30]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 580756Methyl 5-methyl-2-thiophenecarboxylate

Product 1

HCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

N-Bromosuccinimide (Aldrich; 1.70 g, 9.6 mmol) and a catalytic amount of benzoyl peroxide were added to a solution of 5-methyl-thiophene-2-carboxylic acid methyl ester (1.40 g, 9.0 mmol) in chloroform (15 mL). The reaction mixture was stirred under argon at reflux (˜60° C.) for 3 h, then filtered through Celite™ and evaporated under reduced pressure to give 5-bromomethyl-thiophene-2-carboxylic acid methyl ester (2 g) as a yellow oil which was used directly in the next step without further purification.

Workup

  1. filtrationfiltered through Celite™
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a0c459ed62e74cb0a06dc1fcdc0b0e1f
Source dataset
uspto-grants-2010_04
Patent number
US07700632B2

Linked notes

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