4-Chloro-2-(trifluoromethyl)benzonitrile synthesis
- Product Name:4-Chloro-2-(trifluoromethyl)benzonitrile
- CAS Number:320-41-2
- Molecular formula:C8H3ClF3N
- Molecular Weight:205.56
Yield: 63%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 80;
Steps:
115
Add 4-chloro-l-iodo-2-trifluromethylbenzene (1500 mg, 4.89 ?unol), zinc cyanide (345 mg, 2.94 mmol), and tetrakis(triρhenylphosphine)ρa(bǔ)lladium(0) (564 mg, 0.488 mmol) to anhydrous N,N-dimethylformamide (40 mL). Heat to 80 0C overnight. Cool to room temperature, dilute with toluene, wash with 2 N ammonium hydroxide (3x), saturated aqueous sodium chloride, dry, filter, concentrate to give a residue. Chromatograph the residue on silica gel eluting with hexanes/dichloromethane, to give 4- chloro-2-trifluoromethylbenzonitrile (630 mg, 63%): 1H NMR (400 MHz, CDCl3) δ 7.81- 7.78 (m, 2H), 7.67 (dd, IH, J = 8.4, 2.4 Hz).
References:
ELI LILLY AND COMPANY WO2006/44454, 2006, A1 Location in patent:Page/Page column 63
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