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

HRID 217507Notes

Reaction equation

HRID 217507 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=O)C>[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 (200 mg, 0.66 mmol) in DMF (2 mL) was added CuCN (300 mg, 5.0 mmol). The reaction was stirred at 100° C. for 24 hours and then poured into aq. NH3 (40 mL). The mixture was extracted with EtOAc (70 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 5% to 80% EtOAc/hexanes afforded 3-methoxy-5-(trifluoromethyl)benzonitrile. Rf=0.64 (50% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 7.47 (s, 1H), 7.34 (s, 1H), 7.31 (s, 1H), 3.89 (s, 3H).

Workup

  1. extractionThe mixture was extracted with EtOAc (70 mL)
  2. washthe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 5% to 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-88ce170f9dd74dfa8565e8f7cd78ded1
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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