Bromine → Methyl 6-bromo-3-hydroxypicolinate

HRID 595550Notes

Reaction equation

HRID 595550 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-hydroxypicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-hydroxypicolinate (5 g, 32.65 mmol) in 60 mL of H2O was stirred at RT and Br2 (5.22 g, 32.65 mmol) was added dropwise. The mixture was stirred at RT overnight, and the resulting solid was collected and washed with water to afford methyl 6-bromo-3-hydroxypicolinate. Then the filtrate was basified with Na2CO3 until pH reached 7, and after extracted with EtOAc, the organic layer was concentrated to give the 2nd part of methyl 6-bromo-3-hydroxypicolinate (6.1 g total, yield: 80.7%). 1H-NMR (CDCl3, 400 MHz) δ 10.67 (s, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.24 (d, J=4.0 Hz, 1H), 4.02 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. customthe resulting solid was collected
  2. washwashed with water

Sources & evidence

ORD record
ord-a0afbc861a4b4682846eb78eb1c35e6f
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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