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Water → 3-Bromo-2-(difluoromethoxy)-5-methylpyridine

HRID 2271459
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HRID 2271459 반응식
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]([F:19])(S(F)(=O)=O)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C>[Br:1][C:2]1[C:3]([O:9][CH:11]([F:19])[F:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178430683HCID 178430683, 화합물

생성물 1

HCID 904150763-Bromo-2-(difluoromethoxy)-5-methylpyridine수율 71.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매
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실험 절차

To a solution of 3-bromo-5-methylpyridin-2-ol (25.0 g, 0.13 mol) in ACN (100 mL) was added 2,2-difluoro-2-(fluorosulfonyl)acetic acid (23.7 g, 0.13 mol) and sodium carbonate (28.2 g, 0.270 mol). The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the reaction mixture was extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 0-10%, EtOAc/hexanes) afforded the title compound as an off-white solid (22 g, 70%). M+H]=238.09240.09.

후처리

  1. extractionthe reaction mixture was extracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure
  4. customPurification (FCC, SiO2, 0-10%, EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-6892268d82df4041832238829405907f
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09120770B2

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