1: 4-fluoro-l-naphthalene With sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 2 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; cyclohexane T=-78°C; 0.0833333 h;

2-Nitropropane; sodium ethanolate in ethanol T=20°C; 65 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 76 percent / N-fluorobis(phenylsulfonyl)amine / tetrahydrofuran / 2 h / -78 - 20 °C 2.1: 44 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 40 h / 75 °C 3.1: 87 percent / 2-nitropropane; NaOEt / ethanol / 65 h / 20 °C View Scheme

1: 44 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 40 h / 75 °C 2: 87 percent / 2-nitropropane; NaOEt / ethanol / 65 h / 20 °C View Scheme

hydrogenchloride; tin(ll) chloride in diethyl ether

1: N-methylpyrrolidone / 200 °C 2: SnCl2, HCl / diethyl ether View Scheme

1: (i) aq. NaNO2, H2SO4, (ii) HBF4 2: (pyrolysis) 3: N-methylpyrrolidone / 200 °C 4: SnCl2, HCl / diethyl ether View Scheme