聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 4-Chloro-6-(1-(3-fluorophenyl)ethyl)pyrimidine

HRID 1759986笔记

反应方程式

HRID 1759986 反应方程式
[Cl-].C[SiH](C)C.Br[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[CH3:8].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.O>O1CCCC1.BrC(Br)C.[Zn]>[Cl:16][C:17]1[CH:22]=[C:21]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH3:8])[N:20]=[CH:19][N:18]=1

参与物

8

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 709434,6-二氯嘧啶HCID 156802311-(1-溴乙基)-3-氟苯HCID 131723440Tmsci

产物 1

HCID 225998904-Chloro-6-(1-(3-fluorophenyl)ethyl)pyrimidine收率 18.4%

试剂、催化剂与溶剂 3

HCID 112011,1-二溴乙烷催化剂HCID 23994Zinc催化剂HCID 8028四氢呋喃溶剂3 次

实验过程

In 10 ml of tetrahydrofuran was suspended 1.3 g of zinc (powder), to which dibromoethane (2 drops) was added. The mixture was heated under reflux for 5 minutes, to which trimethylsilane chloride was added. The mixture was further heated under reflux for 5 minutes, to which a solution of 2.0 g of 1-(1-bromoethyl)-3-fluorobenzene dissolved in 20 ml of tetrahydrofuran was slowly added with heating under reflux, followed by stirring for 20 minutes. (The solution thus obtained is referred to as solution M). In 10 ml of tetrahydrofuran were suspended 1.5 g of 4,6-dichloropyrimidine and 0.2 g of tetrakistriphenylphosphine palladium, to which the above solution M was added, followed by heating under reflux for 3 hours and further stirring at room temperature for 12 hours. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.43 g of 4-chloro-6-(1-(3-fluorophenyl)ethyl)pyrimidine.

后处理

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperatureThe mixture was further heated
  4. additionwas slowly added
  5. temperaturewith heating
  6. temperatureunder reflux
  7. custom(The solution thus obtained
  8. temperatureby heating
  9. temperatureunder reflux for 3 hours
  10. stirringfurther stirring at room temperature for 12 hours
  11. extractionextracted three times with ethyl acetate
  12. washwashed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated

来源与证据

ORD记录
ord-bcc9aa52e5f64bb3a16802af0883aa90
来源数据集
uspto-grants-2005_01
专利号
US06838463B2

反应笔记

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