Chlorotrimethylsilane → (4-Ethylphenyl)trimethylsilane

HRID 1768560노트

반응식

HRID 1768560 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.[CH3:11][Si:12](Cl)([CH3:14])[CH3:13].[NH4+].[Cl-]>C1COCC1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:4][CH:5]=1)[CH3:10]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 153131-Bromo-4-ethylbenzeneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 1

HCID 280168(4-Ethylphenyl)trimethylsilane수율 93.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
30 °C

실험 절차

Magnesium(9.5 g, 0.39 mole) was suspended in THF (60 mL) at room temperature. A solution of 4-bromo-1-ethylbenzene (49 mL, 0.36 mole) in 300 mL of THF was added dropwise at such a rate as to maintain the temperature between 30° and 60° C. When the addition was complete the reaction mixture was stirred for an additional hour and then cooled to 30° C. Trimethylsilyl chloride (49 mL, 0.39 mole) was added dropwise at such a rate as to maintain the temperature between 30° and 40° C. The thin suspension was stirred overnight at room temperature. Saturated aqueous NH4Cl was added and the reaction mixture partitioned. The aqueous phase was extracted three times with ether, and the combined organic phases were dried (MgSO4) and concentrated. The resultant oil (60 g, 93% yield) was used in the next step without further purification.

후처리

  1. temperatureto maintain the temperature between 30° and 60° C
  2. additionWhen the addition
  3. temperatureto maintain the temperature between 30° and 40° C
  4. stirringThe thin suspension was stirred overnight at room temperature
  5. customthe reaction mixture partitioned
  6. extractionThe aqueous phase was extracted three times with ether
  7. dry with materialthe combined organic phases were dried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9aeb1ca2cefd4046b7d283a5ce4798e1
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378708

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