3-Bromobenzyl bromide → 1-Bromo-3-(but-3-en-1-yl)benzene
反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:12][CH:11]=[CH2:10])[CH:3]=1参加物
4
実験手順
A mixture of 1-bromo-3-(bromomethyl)benzene (1 g, 4.00 mmol) in THF (15 mL) was added allylmagnesium bromide (4.80 mL, 4.80 mmol) and stirred at rt for 1 h, then refluxed for 2 h. It was then quenched with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil. It was then purified by 5% EtOAc/hexane to isolate 1-bromo-3-(but-3-en-1-yl)benzene (0.7 g, 3.32 mmol, 83% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.41-7.31 (m, 2H), 7.21-7.12 (m, 2H), 5.85 (ddt, J=17.1, 10.3, 6.6 Hz, 1H), 5.14-4.94 (m, 2H), 2.75-2.64 (m, 2H), 2.45-2.31 (m, 2H).
後処理
- temperaturerefluxed for 2 h
- customIt was then quenched with NH4Cl
- extractionextracted with EtOAc
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain an oil
- customIt was then purified by 5% EtOAc/hexane
出典と根拠
- ORDレコード
- ord-e1b2300de3c445f3b3b0e10b03029053
- 出典データセット
- uspto-grants-2016_03
- 特許番号
- US09273067B2
反応ノート
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