Reacción #42893

Ecuación de reacción

triethylamine

4-amino-thiophene-3-carboxylic acid methyl ester

chlorofluoroacetyl chloride

→

title compound

4-(2-Chloro-2-fluoro-acetylamino)-thiophene-3-carboxylic acid methyl ester

Disolventes

dichloromethane

methylene chloride

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm up
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   Lavadowashed several times with water
4. 4
   Secadodried with sodium sulfate
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by column chromatography

Procedimiento

To a suspension of 4-amino-thiophene-3-carboxylic acid methyl ester (2 g) in dichloromethane (25 mL) was added chlorofluoroacetyl chloride (1.16 mL) and the reaction mixture was stirred to −15° C. Then a solution of triethylamine (3.2 mL) in dichloromethane (5 mL) was added slowly to the cold reaction mixture which was then allowed to warm up and stirred at room temperature for one hour. The reaction mixture was then diluted with further methylene chloride and washed several times with water, dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a light yellow solid. MS (EI): 251.1; mp=51-54° C.

Fuente