Reaction #40585

Reaction equation

bromine

5-amino-2-methoxypyridine

sodium acetate

sodium thiosulfate

→

expected compound

3-Amino-2-bromo-6-methoxypyridine

Solvents

acetic acid

Conditions

Workup

1. 1
   Otheris prepared
2. 2
   workup.STIRRINGThe reaction mixture is kept stirring for 30 minutes, at room temperature
3. 3
   OtherThe aqueous phase obtained
4. 4
   Extractionis extracted twice with ethyl acetate
5. 5
   DryingThe combined organic phases are dried over magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

A mixture of 1.83 g (14.7 mM) of 5-amino-2-methoxypyridine and 1.21 g (14.7 mM) of sodium acetate in 12 ml of acetic acid is prepared and 0.75 ml (14.7 mM) of bromine is added gently, with stirring and while maintaining at room temperature. The reaction mixture is kept stirring for 30 minutes, at room temperature, and 200 ml of saturated sodium thiosulfate solution are then added. The aqueous phase obtained is extracted twice with ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. 3 g of the expected compound are obtained in the form of a violet-colored solid (quantitative yield).

Source