Chlorotrimethylsilane → (6-Bromo-2,3-difluorophenyl)trimethylsilane

HRID 34020

반응식

HRID 34020 반응식
C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[Br:13][C:14]1[C:15]([Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([F:21])[C:17]([F:20])=[CH:18][CH:19]=1

참가 물질

9

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 676754-Bromo-1,2-difluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 23070109(6-Bromo-2,3-difluorophenyl)trimethylsilane

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

Under nitrogen atmosphere, to a solution of 18.2 mL of N,N-diisopropylamine in 200 mL of tetrahydrofuran was added 66.0 mL of 1.57 M n-butyllithium in hexane at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 20.0 g of 1-bromo-3,4-difluorobenzene in 100 mL of tetrahydrofuran was added dropwise and stirred at this temperature for 30 minutes, stirred at this temperature for 30 minutes, added dropwise with 32.9 mL of chlorotrimethylsilane, and the reaction solution was allowed to warm gradually to room temperature, and stirred for a day. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane)-, to afford 20.3 g of the title compound as a colorless oil.

후처리

  1. additionwas added dropwise
  2. stirringstirred at this temperature for 30 minutes
  3. stirringstirred at this temperature for 30 minutes
  4. temperatureto warm gradually to room temperature
  5. stirringstirred for a day
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified
  10. customseparated by silica gel column chromatography (n-hexane)-

출처 및 근거

ORD 기록
ord-895884dedeb242c3b6988f0654c0ede9
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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