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1,2-Difluoro-4-nitrobenzene → 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole

HRID 2195487
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HRID 2195487 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C([O-])(O)=O.[Na+].[Li+].[Cl-]>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11][C:18]1[CH:17]=[CH:16][C:15]([N+:20]([O-:22])=[O:21])=[CH:14][C:13]=1[F:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 591599466-Bromo-1H-indazol-5-ol

생성물 1

HCID 667671536-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole수율 50.4%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

A mixture of 6-bromo-5-hydroxy-1H-indazole (7.0 g, 33.0 mmol), 3,4-difluoronitrobenzene (4.98 mg, 31.0 mmol), NaHCO3 (2.5 g, 31.0 mmol) in DMF (100 mL) is stirred at 80° C. for 4 hours. Then LiCl (10% aqueous solution) is added and the solution is extracted with EtOAc. The organic phase is dried over anhydrous MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with PE:DCM (1:1) to give the desired product (5.5 g, 46.6% yield). MS (m/z): 354.0 (M+H).

후처리

  1. extractionthe solution is extracted with EtOAc
  2. dry with materialThe organic phase is dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with PE

출처 및 근거

ORD 기록
ord-a8610b737ad041e69731241ff6d2b91e
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE043878E1

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