聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-(3-溴苯基)呋喃-2-甲醛

HRID 446062

反应方程式

HRID 446062 反应方程式
[CH:1]([C:3]1[O:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[Br:11][C:12]1[CH:13]=[C:14](I)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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:11][C:12]1[CH:17]=[C:16]([C:6]2[O:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:15]=[CH:14][CH:13]=1

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 10340Carbonic acid sodium salt (1:2)HCID 115611-溴-3-碘苯HCID 27343555-甲醛基呋喃-2-硼酸

产物 1

HCID 8405175-(3-溴苯基)呋喃-2-甲醛收率 25.9%

试剂、催化剂与溶剂 2

HCID 178418397HCID 178418397，化合物催化剂HCID 8071乙二醇二甲醚溶剂

实验过程

5-Formyl-2-furanboronic acid (676 mg, 4.8 mmol) and 3-bromoiodobenzene (1132 mg, 4 mmol) were dissolved in 1,2-dimethoxyethane (30 mL), tetrakis(triphenylphosphine)palladium (228 mg, 0.2 mmol) was added thereto, 2 mol/L sodium carbonate (9.6 mL) was further added thereto, and the mixture was heated to reflux for 2 hours while stirring. After the reaction was completed water (20 mL) was added thereto, and extraction with ethyl acetate (20 mL×2) was carried out. The organic layer was washed with saturated brine, water was removed using anhydrous sodium sulfate, the solvent was then removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (3/7 (volume ratio)) as an eluent, to give 5-(3-bromophenyl)furan-2-carbaldehyde in a yield of 306 mg (yield 25.9%).

后处理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. additionwas added
  4. extractionextraction with ethyl acetate (20 mL×2)
  5. washThe organic layer was washed with saturated brine, water
  6. customwas removed
  7. customthe solvent was then removed by evaporation under reduced pressure

来源与证据

ORD记录
ord-5e7c749d4a9446d4a9a263f8c69dd32d
来源数据集
uspto-grants-2013_07
专利号
US08476449B2

关联笔记

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