Water → N-(4-bromo-2-methylphenyl)butanamide

HRID 1168004Notes

Reaction equation

HRID 1168004 reaction equation
[C:1]([NH:6][C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Br:14]Br.O>C(O)(=O)C>[Br:14][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[C:8]([CH3:13])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 221809N-(2-Methylphenyl)butanimidic acid

Product 1

HCID 849157N-(4-bromo-2-methylphenyl)butanamideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

30 g of N-butyryl-o-toluidine and 150 g of glacial acetic acid were initially charged at 30° C. A solution of 33 g of bromine in 66 g of glacial acetic acid was added with stirring and then stirring was continued at from 25 to 30° C. for 1 hour. 300 ml of water were then added to the reaction mixture which, after continued stirring for a short time, was filtered, the crystals were washed with water and dried under reduced pressure. 42.5 g (98% yield) of N-(4-bromo-2-methylphenyl)butanamide were obtained in 99.4% purity.

Workup

  1. stirringstirring
  2. stirringafter continued stirring for a short time
  3. filtrationwas filtered
  4. washthe crystals were washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cb27b065bf404f3fb13abd026073b5c2
Source dataset
uspto-grants-2003_09
Patent number
US06620962B2

Reaction notes

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