Reaktion #67634

Reaktionsgleichung

methyl iodide

5-bromo-3-(difluoromethoxy)pyridin-2-ol

→

5-bromo-3-(difluoromethoxy)-2-methoxypyridine

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through diatomaceous earth, which
2. 2
   Waschenwas washed with additional CHCl3
3. 3
   EinengenThe filtrates were concentrated under reduced pressure
4. 4
   Sonstigeto yield an oil which
5. 5
   Sonstigewas purified by silica gel chromatography

Vorschrift

As shown in step 3-v of Scheme 3, 5-bromo-3-(difluoromethoxy)pyridin-2-ol (300 mg; 1.25 mmol) was dissolved in 5 mL of chloroform. Silver carbonate (690 mg; 2.5 mmol) and methyl iodide (780 μL; 1.77 g; 12.5 mmol) were added and the mixture stirred at RT overnight. The reaction mixture was filtered through diatomaceous earth, which was washed with additional CHCl3. The filtrates were concentrated under reduced pressure to yield an oil which was purified by silica gel chromatography to yield 5-bromo-3-(difluoromethoxy)-2-methoxypyridine as a white solid (Compound 1010, 250 mg, 78% yield): ESMS (M+H) 254/256; 1H NMR (CDCl3) δ 8.08 (d, 1H, J=2.1 Hz), 7.56 (d, 1H, J=2.1 Hz), 6.60 (t, 1H, J=75 Hz), 3.98 (s, 3H).

Quelle