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

HRID 1632062Notes

Reaction equation

HRID 1632062 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-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 6-methyl-pyridin-3-ol (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) and stirred for 3 h. The reaction was extracted with ethyl acetate (5×100 mL), washed with brine, dried with Na2SO4, filtered, and concentrated to afford 6.3 g (738%) of I-115 as light yellow solid.

Workup

  1. customThe crude reaction mixture
  2. additionwas poured on
  3. stirringstirred for 3 h
  4. extractionThe reaction was extracted with ethyl acetate (5×100 mL)
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford 6.3 g (738%) of I-115 as light yellow solid

Sources & evidence

ORD record
ord-16eaf0de7829462489b711a2fa49b335
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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