4-Vinylpyridine → 4-[2-(4-Nitro-phenyl)-vinyl]-pyridine

HRID 588026

反応式

HRID 588026 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[CH2:12]>CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

参加物

5

反応物 2

HCID 75024-VinylpyridineHCID 124951-Iodo-4-nitrobenzene

生成物 1

HCID 3071364-[2-(4-Nitro-phenyl)-vinyl]-pyridine収率 37%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To a CH3CN solution of 1-iodo-4-nitrobenzene (498 mg, 2 mmol) and 4-vinylpyridine (262 mg, 2.5 mmol) was added TEA (350 μL, 2.5 mmol) and Pd(OAc)2 (0.45 mg, 0.2 mmol). The mixture was heated to 100° C. for 48 hr in a capped Pyrex tube. It was then cooled to room temperature, quenched with 1N HCl (20 mL) and concentrated under reduced pressure. The mixture was filtered and the solid was taken up in EtOAc (30 mL) and washed with 1N NaOH (30 mL). The organic layer was concentrated, dried over Na2SO4 and concentrated to give 4-[2-(4-nitro-phenyl)-vinyl]-pyridine as yellow solid (160 mg, 37%).

後処理

  1. temperatureIt was then cooled to room temperature
  2. customquenched with 1N HCl (20 mL)
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe mixture was filtered
  5. washwashed with 1N NaOH (30 mL)
  6. concentrationThe organic layer was concentrated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f652f07d23a947f28cac53962537cb21
出典データセット
uspto-grants-2016_01
特許番号
US09227954B2

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