苯乙烯 → 4-[(E)-2-Phenylvinyl]benzo[b]thiophene

HRID 15404

反应方程式

HRID 15404 反应方程式
Br[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1(/[CH:12]=[CH:11]/[C:2]2[C:10]3[CH:9]=[CH:8][S:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参与物

8

反应物 4

HCID 7501苯乙烯HCID 8471三乙胺HCID 80271三(邻甲基苯基)磷HCID 120942084-溴苯并[B]噻吩

产物 1

HCID 231567054-[(E)-2-Phenylvinyl]benzo[b]thiophene

试剂、催化剂与溶剂 3

HCID 167845palladium acetate催化剂HCID 3283乙醚溶剂HCID 6342乙腈溶剂

实验过程

A mixture of 4-bromobenzo[b]thiophene (0.55 g), styrene (0.89 mL), triethylamine (1.81 mL), palladium(II) acetate (59 mg) and tris(2-methylphenyl)phosphine (0.16 g) in acetonitrile (10 mL) was refluxed overnight under an argon atmosphere. The reaction mixture was diluted with diethyl ether and an insoluble material was removed by filtration. The filtrate washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=5/1) to give the title compound (0.56 g).

后处理

  1. temperaturewas refluxed overnight under an argon atmosphere
  2. customan insoluble material was removed by filtration
  3. washThe filtrate washed with 1 mol/L hydrochloric acid, water and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=5/1)

来源与证据

ORD记录
ord-c9b724ccf96a4746a1af2ce58abf5586
来源数据集
uspto-grants-2010_06
专利号
US07732596B2

关联笔记

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