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3-Nitrophenylboronic Acid → 3-(4-Ethoxypyridin-2-yl)nitrobenzene

HRID 1059932
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인쇄 미리보기

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HRID 1059932 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[N+:11]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].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>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:18]2[CH:19]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=[CH:16][CH:17]=2)[CH:7]=1)[CH3:10]
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참가 물질

7

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 5651602-Bromo-4-ethoxypyridine

생성물 1

HCID 186675793-(4-Ethoxypyridin-2-yl)nitrobenzene수율 83.5%

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

To a suspension of 2-bromo-4-ethoxypyridine (879 mg), 3-nitrophenylboronic acid (944 mg) and tetrakis(triphenylphosphine)-palladium (251 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (5.66 ml). The mixture was stirred at 90° C. for 8 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 40 g, 25% ethyl acetate in n-hexane) to give 3-(4-ethoxypyridin-2-yl)nitrobenzene (887 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 40 g, 25% ethyl acetate in n-hexane)

출처 및 근거

ORD 기록
ord-7d342f939d5145d6b4c469e0fb552f81
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06521643B1

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