Réaction #2467962

Équation de réaction

methyl 3-aminothiophene-2-carboxylate

bromine

→

solid

Rendement 33.3%

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

Rendement 33.3%

Solvants

acetic acid

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe reaction mixture was poured into ice cold water
2. 2
   Extractionextracted with chloroform (3×100 mL)
3. 3
   LavageThe combined organic layer was washed with water, brine
4. 4
   Séchagedried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Autreevaporated the solvent
7. 7
   AutreThe residue was chromatographed over silica gel column

Mode opératoire

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.

Source