Reaction #91557

Reaction equation

6-(1,1-dimethylethyl)-3-pyridinol

bromine

→

title compound

2-bromo-6-(1,1-dimethylethyl)-3-pyridinol

Solvents

pyridine

pyridine

brine

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   DryingThe organics were dried over sodium sulphate
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

To a stirred solution of 6-(1,1-dimethylethyl)-3-pyridinol, (3.8 g) in pyridine (150 ml) was added bromine (1.29 ml), diluted in pyridine, dropwise at 20 C. The reaction mixture was allowed to stir at 25-30 C. for 1 h. The reaction had gone to completion by tlc. It was poured into brine and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated under reduced pressure. The crude material was subjected to flash chromatography using a 0-5% gradient of ethyl acetate in hexane to give the title compound, 2.9 g

Source