zinc in sodium hydroxide T=25°C; 2 h;

tert.-butylnitrite; copper(ll) bromide in acetonitrile T=0 - 20°C;

potassium hydroxide in methanol; water 2 h; Heating;

1: 89 percent / sec-butyllithium / cyclohexane; tetrahydrofuran / -75 °C 2: 63 percent / sec-butyllithium; bromine / cyclohexane; tetrahydrofuran / 0.75 h / -75 °C 3: 93 percent / 2,2,6,6-tetramethylpiperidine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 4: 90 percent / potassium hydroxide / methanol; H2O / 2 h / Heating View Scheme

1: 63 percent / sec-butyllithium; bromine / cyclohexane; tetrahydrofuran / 0.75 h / -75 °C 2: 93 percent / 2,2,6,6-tetramethylpiperidine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 3: 90 percent / potassium hydroxide / methanol; H2O / 2 h / Heating View Scheme

1: 93 percent / 2,2,6,6-tetramethylpiperidine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 2: 90 percent / potassium hydroxide / methanol; H2O / 2 h / Heating View Scheme