Methyl iodide → 2-(5-Bromo-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile

HRID 38326노트

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HRID 38326 반응식
[H-].[Na+].[Br:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]([CH:14]([CH3:16])[CH3:15])=[C:8]([CH:13]=1)[O:9][CH2:10][C:11]#[N:12].[CH:19]([O:21][CH2:22]C)=O.IC>>[Br:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]([CH:14]([CH3:16])[CH3:15])=[C:8]([CH:13]=1)[O:9][C:10](=[CH:19][O:21][CH3:22])[C:11]#[N:12]

참가 물질

5

반응물 4

HCID 6328Methyl iodideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 59598690(5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

생성물 1

HCID 670533812-(5-Bromo-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile수율 48.2%

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온도
80 °C

실험 절차

Sodium hydride (0.122 g, 5.0 mmol, 60% w/w) was washed with dry hexanes and evaporated under a stream of nitrogen. 10 mL THF was added and the mixture was cooled to 0° C. (5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.577 g, 2.03 mmol) was added in portions. After 30 min ethyl formate (4.9 mL, 60.9 mmol) was added and the solution was warmed to 80° C. After 4.5 hours the mixture was cooled and 5.0 mL iodomethane was added in one portion. After 16 hours the solution was quenched with H2O, concentrated in vacuo, extracted with ethyl acetate, washed with H2O and then washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (9:1 hexane/ethyl acetate) afforded 2-(5-bromo-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile (0.319 g, 48%) as a white solid.

후처리

  1. customevaporated under a stream of nitrogen
  2. addition10 mL THF was added
  3. additionwas added in portions
  4. temperatureAfter 4.5 hours the mixture was cooled
  5. customAfter 16 hours the solution was quenched with H2O
  6. concentrationconcentrated in vacuo
  7. extractionextracted with ethyl acetate
  8. washwashed with H2O
  9. washwashed with brine
  10. dry with materialThe combined organic layers were dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customPurification via flash chromatography (9:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-3657d13a7fe94bbfb7a63d5ff1265f5c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524725B2

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