3-Bromobenzyl bromide → 1-Bromo-3-(but-3-en-1-yl)benzene

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).

1. temperaturerefluxed for 2 h
2. customIt was then quenched with NH4Cl
3. extractionextracted with EtOAc
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto obtain an oil
8. customIt was then purified by 5% EtOAc/hexane

ORD 기록

ord-e1b2300de3c445f3b3b0e10b03029053

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09273067B2