N-bromobutanimide → 3-(5-Bromomethyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265634Notes

Reaction equation

HRID 1265634 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[CH:12][S:13][C:14]=2[CH3:15])[CH:5]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[CH:12][S:13][C:14]=2[CH2:15][Br:17])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 696892723-(5-Methyl-thiazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 696877023-(5-Bromomethyl-thiazol-4-yl)-benzoic acid methyl esterYield 104.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-(5-methyl-thiazol-4-yl)-benzoic acid methyl ester (2.40 g), N-bromosuccinimid (2.01 g) and α,α′-bis(isobutyronitrile) (0.02 g) in CCl4 (40 mL) was heated at reflux for 30 min. The cooled mixture was filtered and the solvent was evaporated to give crude 3-(5-bromomethyl-thiazol-4-yl)-benzoic acid methyl ester (3.36 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. filtrationThe cooled mixture was filtered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c17ef2d957ae41fcace9579ab5b3c222
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

Loading…