Methyl iodide → (6-Bromo-5-methoxypyridin-2-yl)methanol

HRID 1519426

Reaktionsgleichung

Reaktionsgleichung von HRID 1519426
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:11]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160446662-Bromo-6-(hydroxymethyl)pyridin-3-ol

Produkt 1

HCID 16044667(6-Bromo-5-methoxypyridin-2-yl)methanolAusbeute 156,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-6-(hydroxymethyl)pyridin-3-ol (2.04 g, 10 mmol) and K2CO3 (2.07 g, 15 mmol) in acetone (50 mL) was added iodomethane (1.84 g, 13 mmol) at rt. The reaction mixture was refluxed for 4 h. After that time the reaction was cooled to rt, filtered to remove solids and concentrated under reduced pressure to give (6-bromo-5-methoxypyridin-2-yl)methanol (3.42 g, >99%) as a white solid: 1H NMR (400 MHz, CDCl3): δ 7.25 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.4 Hz, 1H), 4.70 (s, 2H), 3.93 (s, 3H), 2.78 (br s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55bb34e9e2954b129a7f2d432c0df325
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073878B2

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