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

HRID 1952647Notes

Reaction equation

HRID 1952647 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:12])=[CH:8][C:9]=1[C:10]#[N:11])=[O:4].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12][Br:20])=[CH:8][C:9]=1[C:10]#[N:11])=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 682270653-Cyano-5-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682270505-Bromomethyl-3-cyano-thiophene-2-carboxylic acid methyl esterYield 22%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-Cyano-5-methyl-thiophene-2-carboxylic acid methyl ester (0.51 g, 2.81 mmol), NBS (1.05 g, 5.91 mmol), and ACHN (0.032 g, 0.14 mmol) in CCl4 (4 ml) was refluxed in a pressure tube 15 h. The reaction mixture was cooled and evaporated. The residue was purified by column (0-15% EtOAc in hexane) to give 0.16 g (22%) yellow solid.

Workup

  1. temperaturewas refluxed in a pressure tube 15 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customThe residue was purified by column (0-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-33288fc716bf4ab7a1ef37aad521f6a1
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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