반응 #454290

반응 방정식

NaH

benzyl alcohol

3,5-dibromopyridine

→

title product

수율 72.1%

3-benzyloxy-5-bromopyridine

수율 72.1%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hours
2. 2
   기타The mixture was quenched with saturated NH4Cl (500 mL)
3. 3
   workup.ADDITIONdiluted with 400 mL water
4. 4
   추출extracted with Et2O (5×300 mL)
5. 5
   세척The combined Et2O extracts were washed with 50% brine (6×300 mL)
6. 6
   건조dried (MgSO4)
7. 7
   기타The solvent was evaporated in vacuo
8. 8
   기타the crude product was recrystallized from Et2O

실험 절차

NaH (60% in mineral oil) (40.9 g 1.0225 mol) in 800 mL of DMF was cooled to 0° C., and benzyl alcohol (105 mL 1.014 mol) was added slowly. The reaction mixture was stirred for 1 hour at 20° C., then 3,5-dibromopyridine (200.4 g, 846 mmol) was added and the mixture was stirred for 16 hours. The mixture was quenched with saturated NH4Cl (500 mL), diluted with 400 mL water and extracted with Et2O (5×300 mL). The combined Et2O extracts were washed with 50% brine (6×300 mL) and dried (MgSO4). The solvent was evaporated in vacuo and the crude product was recrystallized from Et2O to afford 161 g (72%) of the title product, mp 63-68° C. 1H NMR (CDCl3, 300 MHz) δ 8.37-8.27 (m, 2H), 7.5-7.35 (m, 6H), 5.1 (s, 1H). MS (DCI/NH3) m/z 264, 266 (M+H)+.

출처