Isopropanol → Chloro(chloromethyl)[bis(4-fluorophenyl)]silane

HRID 1980509

반응식

HRID 1980509 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[Cl:10][CH2:11][Si:12]([Cl:15])(Cl)Cl.[CH:16](O)([CH3:18])[CH3:17]>CCOCC>[Cl:15][Si:12]([CH2:11][Cl:10])([C:16]1[CH:18]=[CH:7][C:6]([F:9])=[CH:5][CH:17]=1)[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 99931-Bromo-4-fluorobenzeneHCID 15258Trichloro(chloromethyl)silaneHCID 5462224Magnesium

생성물 1

HCID 13392398Chloro(chloromethyl)[bis(4-fluorophenyl)]silane수율 61%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매4회

실험 절차

A suspension of 7.0 g (0.288 mol) of magnesium turnings in 50 ml of ether was stirred under nitrogen while a solution of 50.2 g (0.287 mol) of 4-bromofluorobenzene in 200 ml of ether was added dropwise at a rate that maintained gentle reflux. After another 2 hours at reflux, the mixture was chilled in ice and a solution of 12.0 ml (0.096 mol) of chloromethyltrichlorosilane in 30 ml of ether was added dropwise. The resulting mixture was refluxed for 4 hours, chilled in ice, treated with a solution of 7.5 ml of isopropanol in 20 ml of ether, stirred 5 minutes, and filtered. The filtrate was evaporated to leave a viscous oil that was stirred with hexanes to give a slurry. Filtration under nitrogen and evaporation of the filtrate left a mobile oil that was distilled to give 17.6 g (61%) of the title compound: bp 100°-140° (0.1 mm); nmr (CDCl3) 3.3 (2H, s), 7.1 (4H, t), 7.7 (4H, d of d).

후처리

  1. additionwas added dropwise at a rate that
  2. temperaturemaintained gentle reflux
  3. temperatureAfter another 2 hours at reflux
  4. temperaturethe mixture was chilled in ice
  5. temperatureThe resulting mixture was refluxed for 4 hours
  6. temperaturechilled in ice
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customto leave a viscous oil that
  10. customto give a slurry
  11. filtrationFiltration under nitrogen
  12. customevaporation of the filtrate
  13. waitleft a mobile oil that
  14. distillationwas distilled

출처 및 근거

ORD 기록
ord-2bf285dc180946349040e574b47bfa9c
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04510136

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