1: 3-trifluoromethyl-fluorobenzene With n-butyllithium; N,N,N',N,-tetramethylethylenediamine; diisopropylamine in tetrahydrofuran T=-78°C; Inert atmosphere; 2: N,N-dimethyl-formamide T=-78°C; Inert atmosphere; Reagent/catalystTemperatureTime; regioselective reaction;

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1: N,N-dimethyl-formamide / 2 h / 90 °C 2: sodium tetrahydroborate; methanol / 2 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C 4: phosphorus tribromide / dichloromethane / 4 h / 0 °C View Scheme

potassium carbonate in ethanol; N,N-dimethyl-formamide T=110°C; sealed tube;