반응 #3405

반응 방정식

NH4Cl

benzyl alcohol

Sodium hydride

3,5-dibromopyridine

→

solid

수율 72.1%

3-Benzyloxy-5-bromopyridine

수율 72.1%

용매

water

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGto stir for 16 hours
2. 2
   추출the mixture was extracted with Et2O (5×300 mL)
3. 3
   세척The combined Et2O extracts were washed with 50% brine (6×300 mL)
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated
6. 6
   기타the residue recrystallized from Et2O

실험 절차

Sodium hydride (60% in mineral oil, 40.9 g, 1.0 mol) in DMF (800 mL) was cooled to 0° C., and benzyl alcohol (105 mL, 1.0 mol) was slowly added. After stirring for 1 hour at ambient temperature, 3,5-dibromopyridine (200.4 g, 846 mmol) was added and the mixture allowed to stir for 16 hours. Saturated NH4Cl solution (500 mL) was added followed by water (400 mL), and the mixture was extracted with Et2O (5×300 mL). The combined Et2O extracts were washed with 50% brine (6×300 mL), dried (MgSO4), concentrated and the residue recrystallized from Et2O to afford a white solid (161 g, 72%): 1H NMR (CDCl3, 300 MHz) δ5.10 (s, 2H), 7.50-7.35 (m, 6H), 8.37-8.27 (m, 2H); MS (CI/NH3) m/z: 264/266 (M+H)+.

출처