海萝胶 → 2-(4-甲氧苯基)吡啶

HRID 16044

反应方程式

HRID 16044 反应方程式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.BrC1C=CC(OC)=CC=1.[Mg].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:5][CH:4]=1

参与物

7

反应物 5

HCID 313海萝胶HCID 77304-溴苯甲醚HCID 79732-溴吡啶HCID 5462224MagnesiumHCID 178491912HCID 178491912，化合物

产物 1

HCID 2202392-(4-甲氧苯基)吡啶

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

That is, as shown in the Reaction Scheme below, (4-methoxyphenyl)magnesium bromide was synthesized from 22.4 g (120 mmol) of 4-bromoanisole by a conventional method by using 3.4 g of magnesium (Mg) in dry tetrahydrofuran (THF) under argon stream and added slowly into a solution of 15.8 g (100 mmol) of 2-bromopyridine and 1.8 g of (1,2-bis(diphenylphosphino)ethane)dichloronickel (II) (Ni(dppe)Cl2) in dry THF and the mixture was refluxed for 1 hour. After adding 250 ml of an aqueous solution of 5% hydrochloric acid to the reaction mixture, the reaction mixture was washed with chloroform. The water layer was neutralized with an aqueous solution of sodium hydrogen carbonate and the objective compound was extracted with chloroform and the organic layer was distilled off under reduced pressure. The distillate immediately solidified at room temperature to obtain 15.1 g (81.5 mmol) of 2-(4-methoxy-phenyl)pyridine (4-MeO-PPy) as white solid. Identification was performed by elementary analysis of C, H and N and 1H-NMR.

后处理

  1. temperaturethe mixture was refluxed for 1 hour
  2. washthe reaction mixture was washed with chloroform
  3. extractionthe objective compound was extracted with chloroform
  4. distillationthe organic layer was distilled off under reduced pressure
  5. customimmediately solidified at room temperature

来源与证据

ORD记录
ord-c4378f80d616422e8c6425299d6ea403
来源数据集
uspto-grants-2010_06
专利号
US07736757B2

关联笔记

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