Diethyl Ether → Methyl 6-bromo-3-hydroxypicolinate

HRID 277143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277143
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 22175135Methyl 6-bromo-3-hydroxypicolinateAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a67842e8f30145169cc0716f478f3f78
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355660B1

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