Iodine → tert-Butyldiphenylchlorosilane

HRID 1274508

반응식

HRID 1274508 반응식
[Mg].II.[C:4](Cl)([CH3:7])([CH3:6])[CH3:5].C([Mg]Cl)(C)(C)C.[C:15]1([Si:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(Cl)[Cl:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu].COCCOC>[C:4]([Si:21]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[Cl:22])([CH3:7])([CH3:6])[CH3:5]

참가 물질

8

반응물 5

HCID 807IodineHCID 6627DichlorodiphenylsilaneHCID 10486tert-BUTYL CHLORIDEHCID 5462224MagnesiumHCID 178418310HCID 178418310, 화합물

생성물 1

HCID 94078tert-Butyldiphenylchlorosilane수율 85%

시약·촉매·용매 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
70 °C

실험 절차

48.6 g (2.0 mol) of magnesium filings and a spatula-tip of iodine are initially introduced into a 2 1 three-necked flask with a precision glass stirrer, straight enclosed-scale thermometer, Dimroth condenser and dropping funnel under a blanket of inert gas. By addition of 600 ml of ethylene glycol dimethyl ether and 203.7 g (2.2 mol) of tert-butyl chloride, tert-butylmagnesium chloride is prepared. Initially 5.2 g (0.02 mol) of copper(II) acetylacetonate and then, at 50° C. over 2 hours, 455.8 g (1.8 mol) of diphenyldichlorosilane are subsequently added dropwise. The internal temperature of the flask rises slightly, and the mixture is subsequently stirred at 70° C. for a further 3 hours to bring the reaction to completion. To remove the precipitated magnesium salt from the solution, the reaction mixture is filtered through a pressure suction filter maintained under an argon atmosphere. The filter cake is rinsed with ethylene glycol dimethyl ether. A concluding fractional distillation of the combined filtrates in vacuo gives 420.6 g of tert-butyldiphenylchlorosilane (85% yield, based on the diphenyldichlorosilane) as a colorless liquid in a GC purity of 92%.

후처리

  1. customis prepared
  2. customthe reaction to completion
  3. customTo remove the precipitated magnesium salt from the solution
  4. filtrationthe reaction mixture is filtered through a pressure suction
  5. filtrationfilter
  6. temperaturemaintained under an argon atmosphere
  7. washThe filter cake is rinsed with ethylene glycol dimethyl ether
  8. distillationA concluding fractional distillation of the combined filtrates in vacuo

출처 및 근거

ORD 기록
ord-cbde98aec9034104afcedb1ef2902e1d
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156918

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