ChemicalBook CAS DataBase List 4-Chloro-2-(trifluoromethyl)benzonitrile

4-Chloro-2-(trifluoromethyl)benzonitrile synthesis

3synthesis methods

Product Name:4-Chloro-2-(trifluoromethyl)benzonitrile
CAS Number:320-41-2
Molecular formula:C8H3ClF3N
Molecular Weight:205.56

23399-77-1
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557-21-1 Synthesis

557-21-1
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4-Chloro-2-(trifluoromethyl)benzonitrile

320-41-2
146 suppliers
$10.00/1g

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