Hydrochloric Acid → 2-Bromo-3-oxo-N-(4-(trifluoromethyl)phenyl)butanamide

HRID 1967639Notes

Reaction equation

HRID 1967639 reaction equation
OO.[O:3]=[C:4]([CH3:19])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:7].[Br-:20].[K+].Cl>C1(C)C=CC=CC=1.O>[Br:20][CH:5]([C:4](=[O:3])[CH3:19])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 253877Potassium BromideHCID 14720783-oxo-N-(4-(trifluoromethyl)phenyl)butanamide

Product 1

HCID 446287412-Bromo-3-oxo-N-(4-(trifluoromethyl)phenyl)butanamideYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Hydrogen peroxide (8.096 ml) was added dropwise to the well stirred solution of 3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide (10 g) [obtained from above step-a], potassium bromide (4.85 g) and conc. HCl (7.446 ml) in toluene (100 ml) at room temperature. Reaction was monitored by TLC. D.M water was added to the reaction mixture and organic layer was separated. Aqueous layer was extracted with ethyl acetate (50 ml×2). Combined organic layer was washed with brine, dried over sodium sulfate and concentrated to give crude compound. The crude was purified by column chromatography to give pure 2-bromo-3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide (6.4 g).

Workup

  1. customReaction
  2. customwas separated
  3. extractionAqueous layer was extracted with ethyl acetate (50 ml×2)
  4. washCombined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give crude compound
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-6c91c6dcf29a424ebd08e67924342df8
Source dataset
uspto-grants-2013_04
Patent number
US08420856B2

Reaction notes

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