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

HRID 34020

反応式

HRID 34020 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)-

出典と根拠

ORDレコード
ord-895884dedeb242c3b6988f0654c0ede9
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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