Hydrochloric Acid → 3-Acetyl-5-(trifluoromethyl)benzonitrile

HRID 906336Notes

Reaction equation

HRID 906336 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:6](N(OC)C)=[O:7])#[N:2].[CH3:19][Mg]Br.Cl>O1CCCC1>[C:6]([C:5]1[CH:4]=[C:3]([CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=1)[C:1]#[N:2])(=[O:7])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866284333-cyano-N-methoxy-N-methyl-5-(trifluoromethyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 673907473-Acetyl-5-(trifluoromethyl)benzonitrileYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyano-N-methoxy-N-methyl-5-(trifluoromethyl)benzamide (196 mg, 0.76 mmol) in anhydrous tetrahydrofuran (2 mL) was added with methylmagnesium bromide (0.96 M solution in ether, 0.95 mL, 0.91 mmol) with stirring on an ice bath, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. Then, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 3-acetyl-5-(trifluoromethyl)benzonitrile (167.4 mg, 100%) as pale yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThen, the organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae4bb7185c7042d987067915f8d89488
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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