Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

HRID 3309

반응식

HRID 3309 반응식
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16](Br)[CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.O>[CH2:3]([O:10][C:16]1[CH:15]=[N:14][CH:13]=[C:12]([Br:11])[CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 693693,5-Dibromopyridine

생성물 1

HCID 153891983-(Benzyloxy)-5-bromopyridine수율 72.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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)+.

후처리

  1. stirringto stir for 16 hours
  2. extractionthe mixture was extracted with Et2O (5×300 mL)
  3. washThe combined Et2O extracts were washed with 50% brine (6×300 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue recrystallized from Et2O

출처 및 근거

ORD 기록
ord-4279b67233d44b409a5090ce4f747f2e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733912

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