N-bromobutanimide → 5-Bromomethyl-3-chloro-thiophene-2-carboxylic acid methyl ester

HRID 1952594Notes

Reaction equation

HRID 1952594 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1[Cl:10])=[O:4].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][Br:19])=[CH:8][C:9]=1[Cl:10])=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18376623Methyl 3-chloro-5-methylthiophene-2-carboxylate

Product 1

HCID 682268765-Bromomethyl-3-chloro-thiophene-2-carboxylic acid methyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-Chloro-5-methyl-thiophene-2-carboxylic acid methyl ester (4.4 g, 23.1 mmol), NBS (5.1 g, 28.85 mmol), and ACHN in CCl4 (40 ml) was refluxed in a pressure tube over the weekend. The reaction mixture was cooled and evaporated. The residue was purified by column (0-5% EtOAc in hexane) to give 3.8 g (61%) yellow solid product.

Workup

  1. temperaturewas refluxed in a pressure tube over the weekend
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customThe residue was purified by column (0-5% EtOAc in hexane)

Sources & evidence

ORD record
ord-f21dff3a896d455eadd4a3bf0f1c33a0
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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