Phenol → 1-Chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene

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A reaction mixture of 2-chloro-5-nitrophenol (50.6 g), anhydrous potassium carbonate (44.5 g), tetrabutylammonium bromide (4.7 g) and 4-bromo-2-methyl-2-butene (53.3 g, 90%) in methyl ethyl ketone (263 mL) was stirred at ambient temperature overnight. TLC of the reaction mixture showed traces of phenol remaining. Additional prenyl bromide (1 mL) was then added to the reaction mixture and stirred for 2 hours. The solvent was then removed from the reaction mixture. The residue of the reaction mixture was then treated with water and extracted into diethyl ether. The extract was washed with 2N sodium hydroxide and water, dried (MgSO4), filtered, and evaporated, to leave a brown solid which was recrystallised from ethyl acetate/isopropyl alcohol to give 1-chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene, 49.5 g, a beige solid, a single spot on TLC (ethyl acetate:hexane, 20:80).

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