Bromine → Methyl 6-bromo-3-hydroxypicolinate

HRID 2178243Notes

Reaction equation

HRID 2178243 reaction equation
[Br:1]Br.[OH:3][C:4]1[C:5]([C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1>O>[Br:1][C:7]1[N:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]([OH:3])=[CH:9][CH:8]=1

Participants

4

Reactant 2

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

Product 1

HCID 22175135Methyl 6-bromo-3-hydroxypicolinateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (5.02 g, 31.4 mmol) was added dropwise to a mixture of methyl 3-hydroxypicolinate (26A) (3.67 g, 26.4 mmol) in water (75 mL) at rt and the mixture was stirred for 2.5 hours. The precipitate was filtered, washed with water and dried in vacuo to provide 4.18 g (75%) of the desired product methyl 6-bromo-3-hydroxypicolinate (26B): 1H NMR (300 MHz, DMSO-d6) δ 10.67 (1H, s), 7.69 (1H, d), 7.42 (1H, d), 3.88 (3H, s).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cfa2eb151af149fd8802dbffba1c2779
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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