copper(l) iodide; sodium iodide; N-methyl-2-(methylamino)ethylamine in 1,4-dioxane T=110°C; 48 h;

1: With n-butyllithium in diethyl ether; hexane T=-78°C; Metallation; 2: With boric acid trimethyl ester in diethyl ether; hexane T=-70 - 10°C; boronation; 3: With hydrogenchloride in diethyl ether; hexane Hydrolysis;

n-butyllithium in diethyl ether; hexane n-BuLi (2.5 M, hexane) was added to C6F2BrH3 iN Et2O at -60 °C,stirring (-60--70 °C, 1 h), 1.5 equiv. of B(OMe)3 was added in E t2O (-70 °C, 30 min), stirring at -60--70 and 20 °C for 1 h and 30-40 min, resp.; poured into 5 percent HCl, org. layer was sepd., aq. layer was extd. with ether, extracts were combined, dried with MgSO4, evapn., recrystn. from hot toluene, elem. anal.;

1: With potassium carbonate; Pd-Tedicyp catalyst in N,N-dimethyl-formamide T=110°C; Heck reaction; 20 h; 2: With sodium hydroxide; water in N,N-dimethyl-formamide T=50 - 80°C;

1: sulfuric acid; nitric acid / 0.5 h / |Cooling with ice 2: anhydrous ammonium carbonate; triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C View Scheme

24 h; Irradiation; Product distribution;

magnesium in tetrahydrofuran Diels-Alder cycloaddition;

n-butyllithium in not given N2 atm.;