ChemicalBook CAS DataBase List 3-CHLOROBENZOYLACETONITRILE

3-CHLOROBENZOYLACETONITRILE synthesis

11synthesis methods

Product Name:3-CHLOROBENZOYLACETONITRILE
CAS Number:21667-62-9
Molecular formula:C9H6ClNO
Molecular Weight:179.6

3-Chlorobenzoylacetonitrile can be synthesized by carbonylation of aryl iodides with Mo(CO)6 in the presence of trimethylsilylacetonitrile and a palladium catalyst.¹

(Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile

107818-32-6
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Yield:21667-62-9 78%

Reaction Conditions:

with sodium hydroxide in water;dimethyl sulfoxide at 25;

Steps:

General Procedure for the Synthesis of β-ketonitriles 3

General procedure: To a solution of 3-chloropropenal (1, 3.0 mmol) in 20 mL of dichloromethane, addedmolecular iodine (3.0 mmol) in one lot and allowed to stir for 3-5 minutes. Then 4 mL of30% aqueous ammonia solution was added to reaction mixture and stirred further for 45minutes. Slight excess of iodine was neutralized with few drops of aqueous sodiumthiosulfate solution and organic layer was evaporated under reduced pressure. DMSO (15mL) was added to solid mass left followed by addition of 3 mL of aqueous NaOH (20 %)maintaining the equilibrium temperature, 25 oC by using water bath. Reaction was monitoredby TLC. After completion of reaction (3-10 minutes), reaction mixture was poured into icecold water and neutralized with dilute HCl. Solid product was filtered, dried andrecrystallized with minimum amount of ethanol.

References:

Sharma, Pawan K.;Kumar, Rajiv;Ram, Sita;Chandak, Navneet [Synthetic Communications,2021,vol. 51,# 12,p. 1847 - 1856] Location in patent:supporting information

2905-65-9 Synthesis