Bromine → Methyl 6-bromo-3-hydroxypicolinate

HRID 423587Notes

Reaction equation

HRID 423587 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 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of methyl 3-hydroxy-2-pyridinecarboxylate (1.69 g, 11.0 mmol) in water (75 mL) at ambient temperature was treated dropwise with bromine (2.39 g, 15.0 mmol). The reaction mixture was stirred at ambient temperature for 3 h, during which time a fine white precipitate formed. The mixture was extracted with CH2Cl2 (100 mL×2). The combined organic extracts were washed with water, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to give 2.11 g (82%) of methyl 6-bromo-3-hydroxy-2-pyridinecarboxylate as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 10.69 (s, 1H), 7.55 (d, 1H, J=8.8 Hz), 7.27 (d, 1H, J=8.8 Hz), 4.04 (s, 3H); LRMS (APCI), m/z 232/234 (M+H).

Workup

  1. customformed
  2. extractionThe mixture was extracted with CH2Cl2 (100 mL×2)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6c7998d890934841b4ee5cccb296955d
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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