Reaktion #70420

Reaktionsgleichung

ammonium chloride

2,5-dibromopyridine

4-(methanesulfonyl)benzyl alcohol

potassium tert-butoxide

→

title compound

Ausbeute 31.0%

5-Bromo-2-(4-methanesulfonylbenzyloxy)pyridine

Ausbeute 31.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Vorschrift

A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%).

Quelle