3-Fluoro-N-methoxy-N-methylbenzamide → 3-Fluoroacetophenone

HRID 1640756노트

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HRID 1640756 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5](N(OC)C)=[O:6].[CH:14]([Mg]Br)=C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:14])[CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 212657573-Fluoro-N-methoxy-N-methylbenzamideHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 99673-Fluoroacetophenone수율 80.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 3-fluoro-N-methoxy-N-methylbenzamide (16 g, 87.4 mmol) in THF (150 mL) was cooled to −78° C. Vinylmagnesium bromide (120 mL, 120 mmol) was added slowly. The mixture was stirred at −78° C. for 10 min, at rt for 3 h, and quenched by addition of 1 N aq HCl (100 mL) at 0° C. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography to afford 1-(3-fluorophenyl)ethanone (9.7 g, yield: 75%) as a colorless oil.

후처리

  1. customquenched by addition of 1 N aq HCl (100 mL) at 0° C
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a8e0d8dbe5a0482da907eb0798b874ff
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114868B2

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