5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE synthesis
- Product Name:5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE
- CAS Number:42518-98-9
- Molecular formula:C5H2Cl2OS
- Molecular Weight:181.04
6310-09-4
42518-98-9
General procedure for the synthesis of 5-chloro-2-thiophene carbonyl chloride from 2-acetyl-5-chlorothiophene: To a mixed solution containing 2-acetyl-5-chlorothiophene (0.161 mg, 1.0 mmol), pyridine (0.012 mL, 0.15 mmol), and chlorobenzene (0.35 mL), at room temperature, disulfur dichloride (S2Cl2, 0.16 mL 2.0 mmol) with continuous stirring. After 2 hours of reaction, sulfuryl chloride (SO2Cl2, 0.121 mL, 1.5 mmol) was added dropwise and stirring was continued for 0.5 hours at room temperature. Subsequently, the reaction mixture was heated to 132 °C and stirred at this temperature for 15 hours. Upon completion of the reaction, the reaction mixture was diluted with deuterated chloroform (CDCl3, 2 mL) and an internal standard (tributyl phosphate, 1BU3PO4, 0.0552 mL, 0.20 mmol) was added for nuclear magnetic resonance (1H NMR) analysis.1H NMR analysis showed an 80% yield of 5-chloro-2-thiophene carbonyl chloride.1H NMR (PhCl. CDCl3, 400 MHz) chemical shift values: δ = 7.99 (d, J = 4 Hz, 1H), 6.86 (d, J = 4 Hz, 1H).
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42518-98-9
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Yield:42518-98-9 100%
Reaction Conditions:
with thionyl chloride;N,N-dimethyl-formamide in dichloromethane for 16 h;Heating / reflux;
Steps:
12.b (b)
32.0 g (0.20 mmol) 5-chloro-thiophene-2-carboxylic acid are 150 ml dichloromethane refluxed for 16 h with stirring with 100 ml of thionyl chloride and 250 μl DMF. The reaction mixture is evaporated down i. vac., the residue in each case is mixed 5 times with toluene and twice with dichloromethane and evaporated down completely. The residue is further reacted directly without any further purification.Yield: quant.C5H2Cl2OS (181.04)
References:
Dahmann, Georg;Gerlach, Kai;Pfau, Roland;Priepke, Henning;Wienen, Wolfgang;Schuler-Metz, Annette;Nar, Herbert US2008/51578, 2008, A1 Location in patent:Page/Page column 39
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42518-98-9
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