Bromine → 6-Bromo-2,4-dimethylpyridin-3-ol

HRID 1662207Notes

Reaction equation

HRID 1662207 reaction equation
[Br:1]Br.[CH3:3][C:4]1[C:9]([OH:10])=[C:8]([CH3:11])[CH:7]=[CH:6][N:5]=1>N1C=CC=CC=1>[Br:1][C:6]1[N:5]=[C:4]([CH3:3])[C:9]([OH:10])=[C:8]([CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 150473662,4-Dimethyl-3-hydroxypyridine

Product 1

HCID 593274926-Bromo-2,4-dimethylpyridin-3-olYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of bromine (4.2 mL, 81.2 mmol) in anhydrous pyridine (80 mL) was added dropwise to a solution of 2,4-dimethyl-3-hydroxypyridine (10.0 g, 81.2 mmol) in anhydrous pyridine (160 mL). The mixture was stirred at room temperature for 1 hour, concentrated under reduced pressure and then further dried under vacuum. The residue was taken up in water (100 mL) and the resulting mixture was stirred for 0.5 hour at room temperature. The precipitated solid was collected by filtration, washed with water and air dried overnight to afford 8.7 g (53%) of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customfurther dried under vacuum
  3. stirringthe resulting mixture was stirred for 0.5 hour at room temperature
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water and air
  6. customdried overnight

Sources & evidence

ORD record
ord-e66b354bdc9d4c5fb28102746def7f27
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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