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

HRID 1057831Notes

Reaction equation

HRID 1057831 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Br:9]Br>N1C=CC=CC=1>[Br:9][C:7]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]([CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 142752-Methyl-5-hydroxypyridineHCID 24408Bromine

Product 1

HCID 119591012-Bromo-6-methylpyridin-3-olYield 53.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 5-hydroxy-2-methylpyridine (8.80 g, 80.6 mmol) in 125 mL of pyridine was added a solution of bromine (14.18 g, 88.7 mmol) in 50 mL pyridine dropwise. The temperature of the reaction mixture rose to 40° C. upon completion of addition. After 1 hour the pyridine was removed under vacuum and the resulting solid was suspended into water (200 mL) and stirred overnight. The solid was collected and dried to give the desire product as a brownish solid (8.05 g, 53.1% yield). 1H NMR (500 MHz, CDCl3): δ2.21 (s, 3H), 6.73 (d, J=8.1 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 9.36 (brs, 1H).

Workup

  1. additionThe temperature of the reaction mixture rose to 40° C. upon completion of addition
  2. customAfter 1 hour the pyridine was removed under vacuum
  3. customThe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-8adbd81cb6c54530899a21b58d10ebc1
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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