3-Fluoro-N-methoxy-N-methylbenzamide → 3-Fluoroacetophenone
反応式
[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]=1参加物
4
反応条件
- 温度
- -78 °C
実験手順
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.
後処理
- customquenched by addition of 1 N aq HCl (100 mL) at 0° C
- extractionThe aqueous layer was extracted with EtOAc (100 mL)
- washThe combined organic phase was washed with brine (50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by column chromatography
出典と根拠
- ORDレコード
- ord-1982f05964284e66832aea53a8f7e9d8
- 出典データセット
- uspto-grants-2014_01
- 特許番号
- US08629138B2
反応ノート
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