1: 2-bromo-1-iodo-4-(trifluoromethyl)benzene With isopropylmagnesium chloride in tetrahydrofuran T=-78°C; Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;

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1: 82 percent / piperidine / toluene / 0.5 h / Heating 2: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min 3: aq. H2SO4, CH3COOH / 24 h / Heating View Scheme

1: 82 percent / piperidine / toluene / 0.5 h / Heating 2: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min 3: aq. H2SO4, CH3COOH / 24 h / Heating 4: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C View Scheme

1: 82 percent / piperidine / toluene / 0.5 h / Heating 2: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min 3: aq. H2SO4, CH3COOH / 24 h / Heating 4: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C 5: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 6: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme

piperidine in toluene 0.5 h; Heating;

1: Methyltriphenylphosphonium bromide With n-butyllithium in hexane T=-78 - 20°C; Wittig Olefination; Inert atmosphere; 2: 2-bromo-4-(trifluoromethyl)benzaldehyde in hexane T=-78 - 20°C; Wittig Olefination; 18 h; Inert atmosphere;