1,3-Dibromopropane → Methyl 2-[4-(3-bromopropoxy)phenyl]acetate

Participants

Reaction Steps

This compound was produced using similar methods as those used Step 3, example 6, starting with (4-hydroxy-phenyl)-acetic acid methyl ester (5.00 g, 30.1 mmol), 1,3-dibromopropane (24.3 g, 120 mmol) and cesium carbonate (40.3 g, 120 mmol). The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give [4-(3-Bromo-propoxy)-phenyl]-acetic acid methyl ester (7.10 g, 82%) as a faint-yellow oil. 1H NMR (400 MHz, DMSO-d6); δ 7.15 (d, 2H), 6.87 (d, 2H), 4.03 (t, 2H), 3.63 (t, 2H), 3.58 (s, 3H), 3.57 (s, 2H), 2.21 (m, 2H).

Provenance & Evidence