Potassium Carbonate → (5-Benzyloxy-biphenyl-3-yl)acetic acid ethyl ester

Participants

Reaction Steps

(3-Benzyloxy-5-bromophenyl)-acetic acid ethyl ester (0.250 g, 0.72 mmol), benzene boronic acid (0.10 g, 0.86 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.04 g, 0.04 mmol) were suspended in a mixture of K2CO3 solution (0.72 ml, 1.44 mmol, 2M aq) and DME (2 ml). This reaction mixture was irradiated in a CEM microwave at 120° C. for 30 min. The reaction mixture was diluted with water and extracted with Et2O (×3). The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give (5-benzyloxy-biphenyl-3-yl)-acetic acid ethyl ester (0.12 g, 0.35 mmol) as a colourless gum in 48% yield. 1H NMR (CDCl3) δ 7.59-7.54 (m, 2H), 7.48-7.30 (m, 8H), 7.13-7.11 (m, 2H), 6.94-6.91 (m, 1H), 5.12 (s, 2H), 4.16 (q, 2H), 3.64 (s, 2H), 1.27 (t, 3H).

Provenance & Evidence