Reaction #409410

Reaction equation

sodium hydrogen carbonate

3-aminothiophenol

triethylamine

methyl 3-bromomethylthiophene-2-carboxylate

→

methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate

Yield 92.3%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   WashThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
3. 3
   Dryinga saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
4. 4
   FiltrationAfter the drying agent was filtered off
5. 5
   Concentrationthe organic layer was concentrated under reduced pressure
6. 6
   OtherThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Procedure

To a solution of 3-aminothiophenol (2.3 g, 18.7 mmol) and triethylamine (3.12 ml, 22.4 mmol) in dichloromethane (30 ml) was slowly added methyl 3-bromomethylthiophene-2-carboxylate (6.24 g, 22.4 mmol) under ice-cooling, followed by stirring for 30 minutes. After the reaction was completed, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give oily methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate (4.82 g, 92%).

Source