Sodium Carbonate → HCID 12085900, compound

Participants

Reaction Steps

To a solution of (E)-1-bromo-2-phenyl-1-(trimethylsilyl)-1-butene (Miller R. B., Al-Hassam, M. I. J. Org. Chem. 1985, 50, 2121-2123) (1) (4.4 g, 15.5 mmol) in DME (50 mL) was added 4-fluorobenzene boronic acid (2.63 g, 18.9 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol), and 2N aqueous sodium carbonate(9.5 mL, 19 mmol). After refluxing overnight the solvent was removed under reduced pressure and the residue was chromatographed (silica gel, hexanes) to give (2) as a white solid (4.2 g, 91%): 1 H NMR (CDCl3) δ 7.30 (m, 3 H), 7.19 (m, 2 H), 7.00 (m, 4 H), 2.12 (q, J=7.7 Hz, 2 H), 0.72 (t, J=7.7 Hz, 3 H), −0.35 (s, 9 H).

Provenance & Evidence