Chloromethyl Methyl Ether → 6-Chloro-2-fluoro-3-(methoxymethoxy)pyridine

HRID 455554노트

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HRID 455554 반응식
[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Cl)[O:17][CH3:18]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([O:9][CH2:16][O:17][CH3:18])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 574756406-Chloro-2-fluoropyridin-3-ol

생성물 1

HCID 574756416-Chloro-2-fluoro-3-(methoxymethoxy)pyridine수율 82.3%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
60 °C

실험 절차

A solution of 6-chloro-2-fluoropyridin-3-ol (1.4 Kg, 9.49 mol) was dissolved in acetone (13 L), and treated with K2CO3 (1574 g, 11.39 mol, 1.2 eq) and MOMCl (840 g, 10.44 mol, 1.1 eq). The mixture was heated at 60° C. for 2 hrs. After cooling to RT, the reaction mixture was filtered to remove inorganic salts. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtOAc/hexanes), affording 6-chloro-2-fluoro-3-(methoxymethoxy)pyridine (1496 g) as a colorless oil in 80% yield over two steps.

후처리

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. customto remove inorganic salts
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (0-10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-24d77b97b9ac422cb61dc1b27eddc73e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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