Iodine → (4-Ethenylphenyl)methyl-diethoxysilane

HRID 497577

반응식

HRID 497577 반응식
[Mg].II.Br[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][Si:14](OCC)([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17].C(C1C=C(O)C(C(C)(C)C)=CC=1O)(C)(C)C>C(OCC)C.CCCCCCC>[CH:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][SiH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:9][CH:8]=1)=[CH2:5]

참가 물질

8

반응물 5

HCID 807IodineHCID 23742,5-Di-tert-butylhydroquinoneHCID 7667beta-BromostyreneHCID 16241TriethoxymethylsilaneHCID 5462224Magnesium

생성물 1

HCID 123242931(4-Ethenylphenyl)methyl-diethoxysilane수율 70.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8900Heptane용매

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온도
2 °C

실험 절차

In a three-neck flask under argon and while being stirred mechanically, 11.7 g (480 mmol) of magnesium chips and some iodine crystals in 40 ml of a solution A (55% diethyl ether, 45% tetrahydrofuran) are mixed together. Then, a solution of 80.0 g (436 mmol) of bromostyrene, dissolved in 210 ml of solvent mixture A, is slowly added in drops, and thus a continuous exothermic reaction is achieved. The solution is stirred under reflux. After the end of the exothermic reaction, the reaction mixture is cooled to 2° C., and then 155.5 g (872 mmol) of methyltriethoxysilane in 160 ml of dry diethyl ether is added; the temperature must not exceed 15° C. After the end of the substitution reaction, stirring is continued at room temperature overnight. Approximately 200 ml of n-heptane is then added, thus the magnesium salts precipitate. The latter are filtered off, 9.7·10−2 g (0.44 mmol) of 2,5-di-tert-butylhydroquinone is added to the filtrate, the solvent is drawn off in a rotary evaporator, and the residue is distilled in fractionated form under vacuum. 72.5 g (307 mmol) of the product was obtained with a yield: 70.3%, and a boiling point of 65-66° C. (0.05 mbar)

후처리

  1. additionis slowly added in drops
  2. customthus a continuous exothermic reaction
  3. stirringThe solution is stirred
  4. temperatureunder reflux
  5. customAfter the end of the exothermic reaction
  6. customexceed 15° C
  7. customAfter the end of the substitution reaction
  8. stirringstirring
  9. customthus the magnesium salts precipitate
  10. filtrationThe latter are filtered off
  11. customthe solvent is drawn off in a rotary evaporator
  12. distillationthe residue is distilled in fractionated form under vacuum

출처 및 근거

ORD 기록
ord-53724010b0a94637818f693fdfd910fe
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949616B2

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