Water → N-(4-bromo-2-chloro-6-(trifluoromethyl)phenyl)-3,3-dimethylbutanamide

HRID 2067778Notes

Reaction equation

HRID 2067778 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4](Cl)=[O:5].[Br:9][C:10]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:13]([NH2:14])=[C:12]([Cl:21])[CH:11]=1.O>C(#N)C>[Br:9][C:10]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:13]([NH:14][C:4](=[O:5])[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])=[C:12]([Cl:21])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 815143,3-Dimethylbutanoyl chlorideHCID 162179374-Bromo-2-chloro-6-(trifluoromethyl)aniline

Product 1

HCID 58097337N-(4-bromo-2-chloro-6-(trifluoromethyl)phenyl)-3,3-dimethylbutanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,3-Dimethylbutanoyl chloride (1.08 g, 8.0 mmol) was added to a solution of 4-bromo-2-chloro-6-(trifluoromethyl)aniline (2.0 g, 7.3 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight. Water was added, and the mixture was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. Purification by column chromatography in dichloromethane afforded the title compound as a powder (1.22 g, 65% over the two steps).

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by column chromatography in dichloromethane

Sources & evidence

ORD record
ord-3b3debf2002b4754ab5cd9e361cc0532
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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