Methanol → Methyl 3-bromocinnamate, predominantly trans
反応式
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[CH3:18]O>>[CH3:18][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]1[CH:15]=[CH:16][CH:17]=[C:7]([Br:6])[CH:8]=1参加物
4
実験手順
Add concentrated sulfuric acid (5.0 mL, 90 mmol) to a solution of 3-bromocinnamic acid (25.0 g, 110 mmol) in MeOH (250 mL). Heat the mixture to reflux for 5 h then cool to room temperature and concentrate under reduced pressure. Dilute the residue with water and extract with EtOAc. Concentrate the combined organic phase under reduced pressure and purify the residue by silica gel chromatography to provide 26 g of trans-3-(3-bromo-phenyl)-acrylic acid methyl ester.
後処理
- temperatureHeat the mixture
- temperatureto reflux for 5 h
- concentrationconcentrate under reduced pressure
- additionDilute the residue with water
- extractionextract with EtOAc
- concentrationConcentrate the combined organic phase under reduced pressure
- custompurify the residue by silica gel chromatography
出典と根拠
- ORDレコード
- ord-dd0fb5823d42412abc408cdcb7cf1514
- 出典データセット
- uspto-grants-2015_07
- 特許番号
- US09079880B2
反応ノート
読み込み中…