Diethyl Ether → Methyl 6-bromo-3-hydroxypicolinate

HRID 584710Notes

Reaction equation

HRID 584710 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.CCOCC>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

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 22175135Methyl 6-bromo-3-hydroxypicolinateYield 70.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mechanically stirred solution of methyl 3-hydroxypicolinate (30.6 g) in water (800 mL) was slowly added bromine (32 g) over a 30 minute period. After the addition was complete, stirring was continued for an additional hour. Ether (300 mL) was added and stirring continued until all the solids had dissolved. The organic layer was separated and the aqueous phase extracted with ether (200 mL). The organic phases were combined, dried (MgSO4) and the solvent evaporated to give 32.8 g of methyl 6-bromo-3-hydroxypicolinate as an off-white solid. Recrystallization from methanol/water gave an analytical sample, m.p. 115-117° C.

Workup

  1. customover a 30 minute
  2. additionAfter the addition
  3. waitwas continued for an additional hour
  4. stirringstirring
  5. dissolutionhad dissolved
  6. customThe organic layer was separated
  7. extractionthe aqueous phase extracted with ether (200 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-1af58ba882054c33b00f5d3952e5823b
Source dataset
uspto-grants-2005_08
Patent number
US06927225B2

Reaction notes

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