Chloromethyl Methyl Ether → 2-Bromo-5-(methoxymethoxy)pyridine

HRID 473379

반응식

HRID 473379 반응식
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][O:13][CH3:14].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:12][O:13][CH3:14])=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27628652-Bromo-5-hydroxypyridine

생성물 1

HCID 574336662-Bromo-5-(methoxymethoxy)pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-bromopyridin-3-ol (25 g, 144 mmol) in DMF (300 mL) at 0° C. under N2 is added portionwise NaH (5.7 g, 144 mmol) over 5 min. The reaction was stirred 1 h, then chloro(methoxy)methane (12 g, 144 mmol) was added and the reaction stirred an additional 1 h at 0° C. Saturated sodium bicarbonate (500 mL) was added slowly and the suspension stirred 30 min and warmed to rt. The solution was extracted with EtOAc (3×400 mL), the combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as a brown oil.

후처리

  1. stirringthe reaction stirred an additional 1 h at 0° C
  2. stirringthe suspension stirred 30 min
  3. extractionThe solution was extracted with EtOAc (3×400 mL)
  4. washthe combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-90dfaf577e2646339ca3f1d911b06b75
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633315B2

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