Methyl iodide → 3-Bromo-4-(methoxymethyl)pyridine

HRID 712636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712636
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[H-].[Na+].[CH3:12]I>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:12]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46840038(3-Bromopyridin-4-yl)methanol

Produkt 1

HCID 667140503-Bromo-4-(methoxymethyl)pyridineAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (3-bromo-pyridin-4-yl)-methanol (300 mg, 1.6 mmol) in THF (50 mL) at 0° C. is added 60% NaH (96 mg, 2.4 mmol). Then the mixture is stirred at room temperature for 30 min. MeI (270 mg, 1.9 mmol) is added to the mixture at 0° C. and again the mixture is stirred at room temperature for 4 hrs. Then the reaction is quenched with saturated NH4Cl aqueous solution and the mixture is extracted with EtOAc. The organic layer is separated, dried and concentrated to give the crude product. Purification by prep-TLC affords 274 mg of 3-bromo-4-methoxymethyl-pyridine.

Aufarbeitung

  1. stirringagain the mixture is stirred at room temperature for 4 hrs
  2. customThen the reaction is quenched with saturated NH4Cl aqueous solution
  3. extractionthe mixture is extracted with EtOAc
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-a6443b9e53f24762bc23e1c1fa59505e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181272B2

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