1-Bromo-2-(bromomethyl)-4-fluorobenzene → HCID 79022360, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-fluorobenzyl bromide (1 g, 3.73 mmol) in THF (15 mL) was added allylmagnesium bromide (5.60 mL, 5.60 mmol) at 0° C. It was warmed to rt and then refluxed for 5 h. The reaction mixture was 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-2-(but-3-en-1-yl)-4-fluorobenzene (0.7 g, 3.06 mmol, 82% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.53-7.45 (m, 1H), 6.99-6.94 (m, 1H), 6.82 (td, J=8.3, 2.9 Hz, 1H), 5.89 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.14-4.98 (m, 2H), 2.89-2.76 (m, 2H), 2.45-2.33 (m, 2H).

Provenance & Evidence