2,3,5-三溴噻吩 → 3-Bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene

HRID 708306

反应方程式

HRID 708306 反应方程式
O.C(=O)([O-])[O-].[Na+].[Na+].[C:8]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].Br[C:22]1[S:23][C:24](Br)=[CH:25][C:26]=1[Br:27]>O.C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:27][C:26]1[CH:25]=[C:24]([C:15]2[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:13][CH:14]=2)[S:23][C:22]=1[C:15]1[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:13][CH:14]=1

参与物

7

反应物 3

HCID 765922,3,5-三溴噻吩HCID 27343204-叔丁基苯硼酸HCID 2735133一水碳酸钠

产物 1

HCID 679735833-Bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene收率 89%

试剂、催化剂与溶剂 3

HCID 178418397HCID 178418397，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂

实验过程

Sodium carbonate monohydrate (58.0 g, 468 mmol) was dissolved in water (500 mL) and a solution of 4-(tert-butyl)-phenylboronic acid (40.0 g) and 2,3,5-tribromothiophene (30.0 g, 94 mmol) in THF (500 mL) was added, and deoxygenated by bubbling with argon. Pd(PPh3)4 (5.0 g, 4.30 mmol) was added and the mixture refluxed for 24 h. The mixture was cooled and the aqueous phase separated and extracted with EtOAc. Organic fractions were combined washed with water (500 mL) and dried over MgSO4. The solvent was evaporated and the crude product washed in MeOH, filtered and dried overnight to afford a light yellow, powdery solid (35.46 g, 89%).

后处理

  1. customdeoxygenated
  2. customby bubbling with argon
  3. temperaturethe mixture refluxed for 24 h
  4. temperatureThe mixture was cooled
  5. customthe aqueous phase separated
  6. extractionextracted with EtOAc
  7. washOrganic fractions were combined washed with water (500 mL)
  8. dry with materialdried over MgSO4
  9. customThe solvent was evaporated
  10. washthe crude product washed in MeOH
  11. filtrationfiltered
  12. customdried overnight

来源与证据

ORD记录
ord-1995a93b609848b0a366d2f4f7a5bf92
来源数据集
uspto-grants-2015_11
专利号
US09176357B2

关联笔记

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