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

HRID 17064Notes

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

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

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

Sources & evidence

ORD record: ord-5b31c4474dcf4fa8bc4e152027450d0f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737295B2

Reaction notes

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