Citric Acid → 3-Bromo-4-methoxypyridine

HRID 1502351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502351
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1F.C[O-].[Na+].CO.C(O)(=O)C[C:16](CC(O)=O)(C(O)=O)[OH:17]>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:17][CH3:16]

Komponenten

5

Edukt 4

HCID 311Citric AcidHCID 887MethanolHCID 27627793-bromo-4-fluoropyridineHCID 10942334Sodium Methoxide

Produkt 1

HCID 6428273-Bromo-4-methoxypyridineAusbeute 40 %

Versuchsvorschrift

3-Bromo-4-fluoropyridine (253 mg, 1.44 mmol) was suspended in a solution of sodium methoxide in methanol (3.0 mL, 4.6 M, 14 mmol) at ambient temperature, the mixture stirred for 3 days, and then poured into aqueous citric acid (1M) and extracted twice into dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil (108 mg, 40%) that was used without further purification. LCMS: M+H+=188 & 190.

Aufarbeitung

  1. extractionextracted twice into dichloromethane
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7bf8516715224028b6f60ca20e949c60
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206175B2

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