Methyltriphenylphosphonium iodide → 1-Bromo-2-ethenyl-4-fluorobenzene

Temperature

0 °C

A mixture of methyltriphenylphosphonium iodide (1.195 g, 2.96 mmol) in tetrahydrofuran (25 mL) was added BuLi (1.182 mL, 2.96 mmol) at 0° C. and stirred at 0° C. for 0.5 h. It was then added 2-bromo-5-fluorobenzaldehyde (0.5 g, 2.463 mmol) and stirred at rt for 16 h. The reaction was then diluted with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 5% EtOAc/hexane to obtain 1-bromo-4-fluoro-2-vinylbenzene (320 mg, 1.592 mmol, 64.6% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.56-7.48 (m, 1H), 7.33-7.23 (m, 1H), 7.09-6.96 (m, 1H), 6.89 (td, J=8.3, 3.1 Hz, 1H), 5.73 (d, J=17.4 Hz, 1H), 5.45 (d, J=11.0 Hz, 1H).

1. extractionextracted with EtOAc
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customto obtain an oil, which
6. customwas then purified by biotage
7. washeluting with 5% EtOAc/hexane

ORD record

ord-1b2727b4761c42c6a3572118fa30243a

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2