Isobutyryl chloride → N-[4-Bromo-3-(trifluoromethyl)phenyl]-2-methylpropanamide

HRID 1390642Notes

Reaction equation

HRID 1390642 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15]>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 678524-Bromo-3-(trifluoromethyl)aniline

Product 1

HCID 21312299N-[4-Bromo-3-(trifluoromethyl)phenyl]-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, cooled solution of 15.0 g. of 4-bromo-3-trifluoromethylaniline in 75 ml. of dry pyridine add 6.8 g. of isobutyrylchloride and heat the resulting mixture at 70° C. for 2 hours. Allow the reaction mixture to cool to room temperature and then pour the mixture into 600 ml. of ice-water, filter and dry the precipitate which is recrystallized from 1:1 petroleum etherdichloromethane to yield 4'-bromo-3'-trifluoromethylisobutyranilide, m.p. 126.5°-128° C.

Workup

  1. temperatureTo a stirred, cooled solution of 15.0 g
  2. additionpour the mixture into 600 ml
  3. filtrationof ice-water, filter
  4. customdry the precipitate which
  5. customis recrystallized from 1:1 petroleum etherdichloromethane

Sources & evidence

ORD record
ord-22e6b65050e64e5d8a6c6caa422b240c
Source dataset
uspto-grants-1979_02
Patent number
US04139638

Reaction notes

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