3-Bromopyridine → 3-[(E)-2-(3-nitrophenyl)vinyl]pyridine

HRID 2230960노트

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HRID 2230960 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-:3])=[O:2].Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:8]/[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 122863-BromopyridineHCID 685143-NitrostyreneHCID 516892Sodium Bicarbonate2회

생성물 1

HCID 227244843-[(E)-2-(3-nitrophenyl)vinyl]pyridine

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

A mixture of 3-nitrostyrene (4.6 ml), 3-bromopyridine (2.6 ml), palladium(II) acetate (0.20 g), tetrabutylammonium chloride (8.4 g) and sodium bicarbonate (6.3 g) in N,N-dimethylformamide (40 ml) was stirred at 110° C. for 3 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isoprbpyl ether to give 3-[(E)-2-(3-nitrophenyl)vinyl]pyridine (5.34 g).

후처리

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isoprbpyl ether

출처 및 근거

ORD 기록
ord-38072d3196fe4c058788c8ee20f28646
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06426345B1

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