2-Methyl-5-hydroxypyridine → 2-Bromo-6-methylpyridin-3-ol

HRID 1715312Notes

Reaction equation

HRID 1715312 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[N:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>N1C=CC=CC=1>[Br:1][C:14]1[C:13]([OH:16])=[CH:12][CH:11]=[C:10]([CH3:9])[N:15]=1

Participants

4

Reactant 2

HCID 142752-Methyl-5-hydroxypyridineHCID 67184N-bromobutanimide

Product 1

HCID 119591012-Bromo-6-methylpyridin-3-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

With cooling with ice, N-bromosuccinimide (18 g) was added to a pyridine (75 ml) solution of 6-methylpyridin-3-ol (10 g), and stirred at room temperature for 4 hours. After further stirred overnight at 50° C., the solvent was evaporated away under reduced pressure. The residue was dissolved in ethyl acetate, and washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water. After dried, the solvent was evaporated away, and the residue was crystallized with chloroform to obtain the entitled compound as a white solid.

Workup

  1. stirringAfter further stirred overnight at 50° C.
  2. customthe solvent was evaporated away under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  5. customAfter dried
  6. customthe solvent was evaporated away
  7. customthe residue was crystallized with chloroform

Sources & evidence

ORD record
ord-572e83f273fd47dda41bd530fbfef4e5
Source dataset
uspto-grants-2010_09
Patent number
US07799820B2

Reaction notes

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