Reaction #4454

Reaction equation

pyridinium hydrobromide

hydrobromic acid

3-methoxy-4-acetylpyridine

→

α-bromo-3-methoxy-4-acetylpyridine hydrobromide

Solvents

acetic acid

acetic acid

acetic acid

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to 17° C.
2. 2
   OtherThe cooling bath was removed and after about thirty minutes a yellow solid
3. 3
   workup.ADDITIONEther (25 mL) was added
4. 4
   Filtrationthe crude α-bromo-3-methoxy-4-acetylpyridine hydrobromide (1.60 g) was collected by filtration
5. 5
   Washwashed with ether and air
6. 6
   Otherdried

Procedure

A solution of pyridinium hydrobromide perbromide (2.33 g, 0.0073 mol) in acetic acid (20 mL) containing 31% hydrobromic acid in acetic acid (1.85 mL) was stirred at room temperature for four hours. The mixture was cooled to 17° C. and a solution of 3-methoxy-4-acetylpyridine (1.02 g, 0.0062 mol) in acetic acid (5 mL) was added. The cooling bath was removed and after about thirty minutes a yellow solid was deposited. Ether (25 mL) was added and the crude α-bromo-3-methoxy-4-acetylpyridine hydrobromide (1.60 g) was collected by filtration washed with ether and air dried.

Source