Carbonic acid sodium salt (1:2) → 3-Isopropenylbenzonitrile

HRID 14082

反应方程式

HRID 14082 反应方程式
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]([CH3:15])=[CH2:14].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[C:13]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([CH3:15])=[CH2:14]

参与物

7

反应物 3

HCID 10340Carbonic acid sodium salt (1:2)HCID 112022-溴丙烯HCID 27343253-氰基苯硼酸

产物 1

HCID 121802503-Isopropenylbenzonitrile

试剂、催化剂与溶剂 3

HCID 178418397HCID 178418397，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8071乙二醇二甲醚溶剂

实验过程

To a stirred solution of 3-cyanophenylboronic acid (10.0 g, 68.05 mmol) dissolved in DME (340 mL) is added 2-bromopropene (6.86 g, 56.7 mmol), and sodium carbonate (62.3 mL of a 2 M solution in water, 124.7 mmol). The reaction mixture is degassed for 20 min with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (2.54 g, 2.2 mmol) is added, the reaction mixture degassed for 10 min, and heated at reflux overnight. The reaction mixture is cooled to room temperature and then partitioned between hexanes and water. The aqueous layer is extracted with hexanes (3×75 mL). The combined organic layers are washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (9:1 hexanes/ethyl acetate) provides the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.96 (m, 1H), 7.85 (d, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.56 (m, 1H) 5.58 (s, 1H), 5.23 (m, 1H), 2.13 (s, 3H).

后处理

  1. customThe reaction mixture is degassed for 20 min with nitrogen
  2. customthe reaction mixture degassed for 10 min
  3. temperatureheated
  4. temperatureat reflux overnight
  5. custompartitioned between hexanes and water
  6. extractionThe aqueous layer is extracted with hexanes (3×75 mL)
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by flash column chromatography (9:1 hexanes/ethyl acetate)

来源与证据

ORD记录
ord-f63263e9904849a6be8ce23d03fbe3dc
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

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