Reaction #91542

Reaction equation

5-hydroxy-2-methylpyridine

bromine

water

→

title compound

2-bromo-6-methyl-3-pyridinol

Solvents

pyridine

pyridine

Conditions

Workup

1. 1
   workup.STIRRINGstirred for a few minutes
2. 2
   Extractionextracted with diethyl ether (4×300 ml)
3. 3
   DryingThe combined organics were dried over sodium sulphate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto give a brown solid that
6. 6
   Otherwas purified through silica using a 0-30% ethyl acetate in hexane system

Procedure

To a solution of 5-hydroxy-2-methylpyridine (Commercial, Aldrich, 44.5 g) in pyridine (400 ml) is added dropwise over 30 min at room temperature a solution of bromine (71.64 g) in pyridine (550 ml). The reaction mixture was stirred for an additional 1.5 h. The reaction mixture was poured into water (4 liters), stirred for a few minutes and extracted with diethyl ether (4×300 ml). The combined organics were dried over sodium sulphate and concentrated in vacuo to give a brown solid that was purified through silica using a 0-30% ethyl acetate in hexane system, to give the title compound as a beige solid, 37 g.

Source