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

HRID 1442519Notes

Reaction equation

HRID 1442519 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 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-cyano-N-methoxy-N-methyl-5-(trifluoromethyl)benzamide (196 mg, 0.76 mmol) in anhydrous tetrahydrofuran (2 mL) stirred on an ice bath was added methylmagnesium bromide (0.96 M solution in ether, 0.95 mL, 0.91 mmol), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with 1 M hydrochloric acid, and extracted with ethyl acetate, and 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 (162 mg, 100%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-936d8c76b53d43078b092efacbe6cff3
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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