1: 1-bromo-4-cyclopropoxy-benzene With n-butyllithium in tetrahydrofuran; diethyl ether; hexane; ethyl acetate T=-78 - -70°C; 0.333333 h; 2: carbon dioxide in tetrahydrofuran; hexane T=-78°C; 0.666667 h; 3: With sodium hydrogen sulphate in tetrahydrofuran; hexane

1.1: sodium carbonate / di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium / toluene / 2.5 h / 100 °C 2.1: diethylzinc / n-heptane; 1,2-dichloro-ethane / 3 h / 0 - 5 °C 3.1: n-butyllithium / ethyl acetate; hexane; diethyl ether; tetrahydrofuran / 0.33 h / -78 - -70 °C 3.2: 0.67 h / -78 °C View Scheme

1.1: diethylzinc / n-heptane; 1,2-dichloro-ethane / 3 h / 0 - 5 °C 2.1: n-butyllithium / ethyl acetate; hexane; diethyl ether; tetrahydrofuran / 0.33 h / -78 - -70 °C 2.2: 0.67 h / -78 °C View Scheme

(i) K2CO3, KI, (ii) /BRN= 1900287/, (iii) aq. KOH; Multistep reaction;