Dimethylformamide → 5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehyde

HRID 34021ノート

反応式

HRID 34021 の反応式
C(NC(C)C)(C)C.[Br:8][C:9]1[C:14]([Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:13]([F:19])[C:12]([F:20])=[CH:11][CH:10]=1.CN(C)[CH:23]=[O:24]>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[Br:8][C:9]1[C:14]([Si:15]([CH3:16])([CH3:17])[CH3:18])=[C:13]([F:19])[C:12]([F:20])=[C:11]([CH:10]=1)[CH:23]=[O:24]

参加物

8

反応物 3

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 23070109(6-Bromo-2,3-difluorophenyl)trimethylsilane

生成物 1

HCID 230701765-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehyde

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 containing 6.34 mL of N,N-diisopropylamine in 100 mL of tetrahydrofuran, 26.4 mL of 1.57 Mn-butyllithium in hexane was added at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 10.0 g of (6-bromo-2,3-difluorophenyl)trimethylsilane in 100 mL of tetrahydrofuran was added dropwise, stirred at this temperature for 1 hour, then added dropwise with 2.92 mL of N,N-dimethylformamide, allowed to gradually warm to room temperature, and stirred fro 3 hours. 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 9.70 g of the title compound as a colorless oil.

後処理

  1. additionwas added at 0° C.
  2. additionwas added dropwise
  3. stirringstirred at this temperature for 1 hour
  4. temperatureto gradually warm to room temperature
  5. stirringstirred fro 3 hours
  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-ffc56b65863d460a9838b0858a75ec3d
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

反応ノート

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