2,3-Dichlorobenzoyl cyanide synthesis
- Product Name:2,3-Dichlorobenzoyl cyanide
- CAS Number:77668-42-9
- Molecular formula:C8H3Cl2NO
- Molecular Weight:200.02
2905-60-4
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1. Synthesis of 2,3-dichlorobenzoyl cyanide 2,3-Dichlorobenzoyl chloride (20.0 g, 100 mmol) and cuprous iodide (I) (0.90 g, 4.7 mmol) were suspended in acetonitrile (50 mL) and stirred at room temperature until a yellow homogeneous solution was formed. Solid sodium cyanide (5.15 g, 110 mmol) was added slowly with a controlled addition time of 5-8 hours. After addition, stirring of the reaction mixture was continued for 1 h. The reaction progress was monitored by HPLC. The resulting inorganic salt (mainly NaCl) was removed by filtration and the filter cake was washed with acetonitrile (15 mL). Acetonitrile was removed by distillation under reduced pressure (~150 mbar). Sodium metabisulfite (Na2S2O3, 0-4 g, 3 mmol) was added to remove trace iodine. Finally, the product was purified by vacuum distillation (jacket temperature 140°C, boiling point 115°C/2 mbar) to give 2,3-dichlorobenzoyl cyanide in >80% yield and 100% purity (as determined by analytical HPLC) with a melting point of 60°C.
Yield:77668-42-9 94.2%
Reaction Conditions:
at 160 - 165; for 7 h;
Steps:
6
Example 6: Synthesis of 2,3-dichlorobenzoyl cyanide; A reactor was loaded with 350.0 g of 2,3-dichlorobenzoyl chloride (1.67 moles) and 200.0 g of cuprous cyanide. The mixture was heated to 160-165 0C and stirred at this temperature for 7 hours. The mixture was cooled to 85 0C and 1200 ml of toluene was added to the mixture. The mixture was stirred for 1 hour at 60 0C, cooled to 15 0C and the inorganic salts were filtrated. The solvent toluene was distilled from the filtrate at 55 0C under reduced pressure. The crude product was crystallised from petroleum ether giving 323.3 g of 2,3-dichlorobenzoyl cyanide with an assay of 97.4 %. Yield was 94.2 %.
References:
CALAIRE CHIMIE SAS WO2007/138075, 2007, A1 Location in patent:Page/Page column 14
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