Phenylacetylene → 1,4-Bis(phenylethynyl)-2,5-dimethoxybenzene

HRID 7196

反応式

HRID 7196 の反応式
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5](Br)=[CH:4][C:3]=1[O:11][CH3:12].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1CCCCC1.[Cu](I)I>[C:13]1([C:19]#[C:20][C:2]2[CH:7]=[C:6]([O:8][CH3:9])[C:5]([C:20]#[C:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:4][C:3]=2[O:11][CH3:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 2

HCID 10821PhenylacetyleneHCID 2312401,4-Dibromo-2,5-dimethoxybenzene

生成物 1

HCID 126604771,4-Bis(phenylethynyl)-2,5-dimethoxybenzene収率 75.7%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8082Piperidine溶媒

反応条件

温度
80 °C

実験手順

50 g (160 mmol) of 1,4-dibromo-2,5-dimethoxy benzene, 3.6 g (0.005 mol) of bistriphenylphosphine palladium dichloride and 0.97 g (0.005 mol) of copper iodide were put into a 1 litter 3-neck flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and dissolved in 500 ml of piperidine. 43 g (0.422 mol) of phenylacetylene was then slowly added dropwise at room temperature. The reaction temperature was slowly raised to 80° C. and then the reaction mixture was stirred at the same temperature for 12 hours. When the reaction was completed, the reaction mixture was cooled down to room temperature, and then generated salt was filtered off. The solvent was removed under a reduced pressure, and then the residue was extracted with methylene chloride. Organic layer was washed with water several times and dried with anhydrous magnesium sulfate, and then the solvent was removed to obtain yellow solid. This solid was recrystallized from ethyl acetate to obtain yellow crystal, which was sufficiently dried in a vacuum oven at 40° C. to give 41 g (yield: 72%) of the desired product, and its melting point was 172° C.–174° C.

後処理

  1. customequipped with a stirrer
  2. temperaturethe reaction mixture was cooled down to room temperature
  3. filtrationwas filtered off
  4. customThe solvent was removed under a reduced pressure
  5. extractionthe residue was extracted with methylene chloride
  6. washOrganic layer was washed with water several times
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was removed
  9. customto obtain yellow solid
  10. customThis solid was recrystallized from ethyl acetate
  11. customto obtain yellow crystal, which
  12. customwas sufficiently dried in a vacuum oven at 40° C.

出典と根拠

ORDレコード
ord-69e50f4a0a4148ad88f1efb062fdfe32
出典データセット
uspto-grants-2006_08
特許番号
US07084231B2

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