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A mixture of 2.6 g (10 mmol) of 2-[(5-bromopentyl)oxy]phenol, 1.8 g (12 mmol) of methyl bromoacetate, 4.4 g (32 mmol) of anhydrous granular potassium carbonate, and 60 mL of dry acetonitrile was stirred and refluxed for 20 hr. The mixture was cooled and filtered with suction. The solids were washed with ether and the filtrate and washes were combined and concentrated in vacuo. The oily residue was purified by flash chromatography on silica gel, eluting with 3:1 hexane-ether. There was obtained 2.2 g (66.5%) of [2-[(5-bromopentyl)oxy]phenoxy]acetic acid methyl ester as an oil.

1. temperaturerefluxed for 20 hr
2. temperatureThe mixture was cooled
3. filtrationfiltered with suction
4. washThe solids were washed with ether
5. concentrationconcentrated in vacuo
6. customThe oily residue was purified by flash chromatography on silica gel
7. washeluting with 3:1 hexane-ether