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

HRID 2230960ノート

反応式

HRID 2230960 の反応式
[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]

参加物

7

反応物 3

HCID 122863-BromopyridineHCID 685143-NitrostyreneHCID 516892Sodium Bicarbonate2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-38072d3196fe4c058788c8ee20f28646
出典データセット
uspto-grants-2002_07
特許番号
US06426345B1

反応ノート

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