1-bromo-4-ethenyl-2-fluorobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-bromo-2-fluoro-4-iodo-benzene (1 g, 3.32 mmol), tributyl(vinyl)tin (0.97 mL, 3.32 mmol) and dichlorobis(triphenylphosphine)palladium(II) (116 mg, 0.17 mmol) in anhydrous DMF (3 mL) was heated in a microwave reactor to 160° C. for 5 minutes. Ether (20 mL) and H2O (5 mL) were added and partitioned. The organic layer was washed with water, brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with hexanes to provide the title compound as a colorless oil (360 mg, 54%). 1H NMR (300 MHz, CDCl3) δ 5.33 (d, J=9 Hz, 1 H), 5.76 (d, J=18 Hz, 1 H), 6.63 (dd, J=18 Hz, J=9 Hz, 1 H), 7.05 (dd, J=9 Hz, J=1 Hz, 1 H), 7.16 (dd, J=9 Hz, J=1 Hz, 1 H), 7.49 (t, J=9 Hz, 1 H); (DCl/NH3) m/z 201 (M+H)+. partitioned The organic layer was washed with water, brine dried (MgSO4) filtered concentrated The residue was chromatographed on silica gel eluting with hexanes