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3-Nitrophenylboronic Acid → 3-(3-Trifluoromethylpyridin-2-yl)nitrobenzene

HRID 1059911
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인쇄 미리보기

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HRID 1059911 반응식
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([C:19]2[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=[CH:17][CH:18]=2)=[N:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

7

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 186675723-(3-Trifluoromethylpyridin-2-yl)nitrobenzene수율 50.5%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 8071
1,2-Dimethoxyethane
용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a suspension of 2-chloro-3-trifluoromethylpyridine (908 mg), 3-nitrophenylboronic acid (1.09 g) and tetrakis(triphenylphosphine)-palladium (289 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (6.5 ml). The mixture was stirred at 80° C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, ethyl acetate:n-hexane=20:80 to 25:75) to give 3-(3-trifluoromethylpyridin-2-yl)-nitrobenzene (677 mg).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 50 g, ethyl acetate:n-hexane=20:80 to 25:75)

출처 및 근거

ORD 기록
ord-edd2d6c8e3234ffdac56ae061e963283
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06521643B1

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