4-(3-Bromopropoxy)1-phenoxybenzene → 2-Phenoxy-3-[4-(4-phenoxy phenoxy)propoxyphenyl]propanoic acid methyl ester

Participants

Reaction Steps

A mixture of 3-(4-hydroxyphenyl)-2-phenoxypropanoic acid methyl ester (0.055 g, 0.18 mmol) with 1-(3-bromopropoxy)-4-phenoxybenzene (Step A) (0.055 g, 0.18 mmol) and potassium tert-butoxide (0.020 g, 0.18 mmol) were stirred in DMF (5 mL) overnight. The mixture reaction concentrated in vacuo with toluene (2 times), reconstituted in Ethyl acetate and washed with water (3 times) and brine, dryed (Na2SO4) and concentrated to afford a crude product that was purified by chromatographied in silicagel (hexanes/Ethyl acetate, 3:1) to give 0.022 g of the title compound (23%). 1H-NMR (200.15 MHz, CDCl3): δ 7.34–7.15 (m, 6H), 7.07–6.71 (m, 12H), 4.80–4.68 (m, 1H), 4.13 (t, 4H, J=15.1), 3.71 (s, 3H), 3.20–3.15 (m, 2H), 2.30–2.18 (q, 2H).

Provenance & Evidence