Reacción #2467962

Ecuación de reacción

methyl 3-aminothiophene-2-carboxylate

bromine

→

solid

Rendimiento 33.3%

Methyl 3-amino-4-bromothiophene-2-carboxylate

Rendimiento 33.3%

Disolventes

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was poured into ice cold water
2. 2
   Extracciónextracted with chloroform (3×100 mL)
3. 3
   LavadoThe combined organic layer was washed with water, brine
4. 4
   Secadodried over sodium sulfate
5. 5
   FiltraciónThe solution was filtered
6. 6
   Otroevaporated the solvent
7. 7
   OtroThe residue was chromatographed over silica gel column

Procedimiento

To a solution of methyl 3-aminothiophene-2-carboxylate (1 g, 6.36 mmol) in acetic acid (10 mL) was added a solution of bromine (0.32 mL, 6.36 mmol) in acetic acid (1 mL) slowly for 5 min at rt and stirred at the same temperature for 16 h. The reaction mixture was poured into ice cold water and extracted with chloroform (3×100 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (95:5) as eluents to give the product as a pale yellow color solid (0.5 g, 33%), mp 58-60° C.

Fuente