Bromine → Methyl 6-bromo-3-hydroxypicolinate

HRID 2201513Notes

Reaction equation

HRID 2201513 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:12]Br>O>[Br:12][C:5]1[N:4]=[C:3]([C:8]([O:10][CH3:11])=[O:9])[C:2]([OH:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 22175135Methyl 6-bromo-3-hydroxypicolinateYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-hydroxypicolinate (5.0 g, 32.65 mmol) in H2O was stirred at RT and then Br2 (5.2 g, 32.65 mmol) was added dropwise. After the mixture was stirred at RT overnight, the mixture was filtered and the precipitate was washed with water and dried to give methyl 6-bromo-3-hydroxypicolinate (6.1 g, yield 80.7%). 1H-NMR (DMSO, 400 MHz) δ 10.71 (s, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 3.87 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. stirringAfter the mixture was stirred at RT overnight
  2. filtrationthe mixture was filtered
  3. washthe precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-7a1c2969754e4d288030a991f1db102f
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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