聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 反-4'-(4-正丙基环己基)-3,4-二氟-1,1-联苯

HRID 1181

反应方程式

HRID 1181 反应方程式
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([Si](OC)(OC)OC)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:41][C:42]1[CH:43]=[C:44](Br)[CH:45]=[CH:46][C:47]=1[F:48].O>C1(C)C=CC=CC=1.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>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:45]3[CH:44]=[CH:43][C:42]([F:41])=[C:47]([F:48])[CH:46]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

参与物

7

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 676751-溴-3,4-二氟苯HCID 2724141四丁基氟化铵HCID 108602534-(4-Propylcyclohexyl)-phenyltrimethoxysilane

产物 1

HCID 612306反-4'-(4-正丙基环己基)-3,4-二氟-1,1-联苯收率 94.5%

试剂、催化剂与溶剂 2

HCID 178418397HCID 178418397，化合物催化剂HCID 1140甲苯溶剂3 次

实验过程

To 0.645 g (2 mmol) of 4-(4-propylcyclohexyl)-phenyltrimethoxysilane (Ih) was added 2.1 ml of TBAF (2.1 mmol, 1M in THF) under nitrogen, and the mixture was stirred at room temperature for 30 minutes. After the solvent was removed under reduced pressure, a solution of 3,4-difluorobromobenzene (0.463 g, 2.4 mmol) in toluene (1 ml) was added, followed by the addition of a suspension of tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) in toluene (3 ml). The resulting mixture was refluxed for 3 hours. After cooling, to the reaction mixture were added water and toluene. The organic layer was separated and the aqueous layer was extracted with toluene three times. The combined organic layer was dried over magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane) to obtain 0.594 g (40%) of white crystals.

后处理

  1. customAfter the solvent was removed under reduced pressure
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. temperatureAfter cooling, to the reaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with toluene three times
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. customAfter the magnesium sulfate was removed by filtration
  8. customthe filtrate was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (heptane)

来源与证据

ORD记录
ord-f5c19c1716b641f7a3721e4238a2fc65
来源数据集
uspto-grants-1998_03
专利号
US05723621

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