聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 1-(Phenylethynyl)-4-(phenylsulfonyl)benzene

HRID 1351663

反应方程式

HRID 1351663 反应方程式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]1([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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 8471三乙胺HCID 11575碘苯HCID 199393204-Phenylsulfonylphenylethyne

产物 1

HCID 210994031-(Phenylethynyl)-4-(phenylsulfonyl)benzene收率 28%

试剂、催化剂与溶剂 3

HCID 24350碘化亚铜催化剂HCID 178418476HCID 178418476，化合物催化剂HCID 1140甲苯溶剂

实验过程

A mixture of 1-ethynyl-4-(phenylsulfonyl)benzene (100 mg, 0.4 mmol), iodobenzene (0.05 mL, 0.44 mmol) and triethylamine (1 mL) in toluene (1 mL) was degassed. Copper(I) iodide (3 mg, 0.004 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (3 mg, 0.004 mmol) were added and the reaction stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (35 mg, 28%). δH (500 MHz, d6 DMSO): 7.97 (4H, dd, J=2.6, 8.4 Hz), 7.77–7.69 (3H, m), 7.64–7.56 (4H, m), 7.43–7.41 (3H, m).

后处理

  1. customwas degassed
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

来源与证据

ORD记录
ord-8973bec5db5f4dee8b621d09f2ec6299
来源数据集
uspto-grants-2007_05
专利号
US07217740B2

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