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

HRID 1632012Notes

Reaction equation

HRID 1632012 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9]Br>N1C=CC=CC=1>[Br:9][C:6]1[C:5]([OH:8])=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 142752-Methyl-5-hydroxypyridineHCID 24408Bromine

Product 1

HCID 119591012-Bromo-6-methylpyridin-3-olYield 146.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 6-methyl-pyridin-3-ol (I-1, Y═CH3, 5.0 g, 45.82 mmol) in pyridine (15 mL) was added bromine (3.66 g, 22.91 mmol). The reaction was stirred at room temperature under N2 for 20 h. The crude reaction mixture was poured on to crushed ice-water (300 mL), stirred for 3 h. The mixture was extracted with ethyl acetate (5×100 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to afford 6.3 g (73%) of 2-bromo-6-methyl-pyridin-3-ol (I-2, X═Br, Y═CH3) as light yellow solid.

Workup

  1. customThe crude reaction mixture
  2. additionwas poured on
  3. stirringstirred for 3 h
  4. extractionThe mixture was extracted with ethyl acetate (5×100 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e0a58bf31a864f239382acc1cd437624
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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