碳酸钾 → 9-苯基蒽

HRID 537591

反应方程式

HRID 537591 反应方程式
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[C:16]1([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参与物

7

反应物 4

HCID 11430碳酸钾HCID 66827苯硼酸HCID 740629-BromoanthraceneHCID 80271三(邻甲基苯基)磷

产物 1

HCID 117669-苯基蒽收率 85%

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 8071乙二醇二甲醚溶剂

反应条件

温度
80 °C

实验过程

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylboronic acid, 60 mg (0.21 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2), 10 mL (20 mmol) of a potassium carbonate aqueous solution (2 mol/L), 263 mg (0.84 mmol) of tris(ortho-tolyl)phosphine (abbreviation: P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME) were put in a 200 mL three neck flask, and then stirred for nine hours at 80° C. in nitrogen stream. After reaction, a precipitated solid was collected by suction filtration. Subsequently, the solid was dissolved in toluene and then filtered through florisil, celite, and alumina. After a filtrate was washed with water and saturated saline, it was dried with magnesium sulfate. After the mixture was subjected to natural filtration, when the filtrate was concentrated, 21.5 g of 9-phenylanthracene which was a target substance was obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1)).

后处理

  1. customAfter reaction
  2. filtrationa precipitated solid was collected by suction filtration
  3. dissolutionSubsequently, the solid was dissolved in toluene
  4. filtrationfiltered through florisil, celite, and alumina
  5. washAfter a filtrate was washed with water and saturated saline, it
  6. dry with materialwas dried with magnesium sulfate
  7. filtrationAfter the mixture was subjected to natural filtration, when the filtrate
  8. concentrationwas concentrated
  9. customwas obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1))

来源与证据

ORD记录
ord-4e389874e59f47cf8a297b6f7d703899
来源数据集
uspto-grants-2014_10
专利号
US08860019B2

关联笔记

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