Sodium Hydroxide → 6-Bromo-2-fluoropyridin-3-ol

HRID 335952

Reaktionsgleichung

Reaktionsgleichung von HRID 335952
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].[Br:11]Br.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.CCOC(C)=O.O>[Br:11][C:4]1[N:3]=[C:2]([F:1])[C:7]([OH:8])=[CH:6][CH:5]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 27627852-Fluoro-3-hydroxypyridine

Produkt 1

HCID 299198756-Bromo-2-fluoropyridin-3-olAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Fluoropyridin-3-ol (5.96 g, 52.7 mmol) was suspended in acetic acid and cooled in an ice bath. NaOH (10.0 N, 6.0 mL, 60.0 mmol) was added and the mixture stirred for 10 min. Bromine (2.8 mL, 54.4 mmol) was added dropwise and the mixture stirred for 20 min. Sodium sulfite (1.4 g) was added and the mixture stirred for 10 min. Water (400 mL) and EtOAc (400 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to ethyl acetate gradient) gave the desired 6-bromo-2-fluoropyridin-3-ol (3.67 g, 19.12 mmol, 36.3% yield) MS m/z=192.0, 194.0 [M+H]+. Calculated for C5H3BrFNO: 190.94.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringthe mixture stirred for 20 min
  3. stirringthe mixture stirred for 10 min
  4. additionthe phases mixed
  5. customseparated
  6. dry with materialThe organic was dried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-2dfd1a72bb654e8fa0524e3d30875bee
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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