Ammonia → 3-Methoxy-5-(trifluoromethyl)benzonitrile

HRID 873080Notes

Reaction equation

HRID 873080 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([O:12][CH3:13])[CH:3]=1.[C:14]([Cu])#[N:15].N>CN(C)C=O>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 197731061-Iodo-3-methoxy-5-(trifluoromethyl)benzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 269863073-Methoxy-5-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-iodo-3-methoxy-5-(trifluoromethyl)benzene (2.23 g, 7.38 mmol) in N,N-dimethylformamide (DMF) (20 mL) was added CuCN. The reaction mixture was stirred at 100° C. for 24 h, and then poured into aq. NH3 (100 mL) and extracted with ethyl acetate (100 mL). Separated organic portions were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. Purification via flash chromatography (ethylacetate/hexanes: 5% to 80%) afforded the title product (1.3 g).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washSeparated organic portions were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash chromatography (ethylacetate/hexanes: 5% to 80%)

Sources & evidence

ORD record
ord-b5974efec5bd4873b4d3eb5c564b51ea
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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