2-(Chloromethyl)thiophene synthesis
- Product Name:2-(Chloromethyl)thiophene
- CAS Number:765-50-4
- Molecular formula:C5H5ClS
- Molecular Weight:132.61
636-72-6
765-50-4
The general procedure for the synthesis of 2-chloromethylthiophene from 2-thiophenemethanol was as follows: 2-thiophenemethanol (5,58 g, 509 mmol) and pyridine (60 g, 763 mmol) were dissolved in 600 mL of anhydrous dichloromethane at 0 °C, and thionyl chloride was added slowly and dropwise. The reaction mixture was stirred at 0°C for 1 hour, then brought to room temperature and continued to stir overnight. Upon completion of the reaction, the reaction was quenched by the addition of 500 mL of water. The organic layer was separated and the aqueous layer was extracted twice with 300 mL of dichloromethane. The organic layers were combined and washed sequentially with 600 mL of 5% aqueous sodium bicarbonate and 300 mL of brine. The organic layer was dried with anhydrous sodium sulfate and concentrated to give 40 g of 2-chloromethylthiophene (6) as an oil in 60% yield.
Yield:765-50-4 203 mg
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in dichloromethane at 0 - 20;
Steps:
2-(Chloromethyl)thiophene
A solution ofthiophen-2-ylmethanol (200 mg, 1.75 mmol), diisopropylethylamine (DIEA,453 mg, 612 )lL, 3.5 mmol) in DCM (5 mL) was cooled to 0 °C, MsCl (163 )lL, 2.1 mmol) wasadded and the mixture warmed to RT. After 2 h H20 and DCM were added, the organic layerseparated and washed with sat. NH4Cl, H20, sat. NaHC03, dried with MgS04 and concentrated togive the title compound (203 mg, light brown oil) which was used without purification MS m/z25 133 (MH+).
References:
F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;HAN, Xiaochun;LOU, Yan;MICHOUD, Christophe;MISCHKE, Steven Gregory;REMISZEWSKI, Stacy;RUPERT, Kenneth Carey WO2014/9495, 2014, A1 Location in patent:Page/Page column 44
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