bromine; anhydrous iron chloride T=40°C; 34 h; Industry scale;

1: iron; aqueous NH4Cl 3: iron; bromine View Scheme

1: sulfuric acid; aqueous phosphoric acid; nitrosylsulfuric acid / anschliessendes Behandeln mit Natriumhypophosphit-Loesung und Kupfer(I)-oxid 2: iron; aqueous NH4Cl 4: iron; bromine View Scheme

2: iron; bromine View Scheme

1: H2SO4; HNO3 2: sulfuric acid; aqueous phosphoric acid; nitrosylsulfuric acid / anschliessendes Behandeln mit Natriumhypophosphit-Loesung und Kupfer(I)-oxid 3: iron; aqueous NH4Cl 5: iron; bromine View Scheme

bromine; iron

1: With n-butyllithium in diethyl ether; hexane T=-75°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 ethereal soln. of C6F3BrH2 at -60 °C, keeping at this temp., 1.5 equiv. of cold (-70 °C) B(OMe)3 was added in ether, mixt. was stirred for 1 h at -60 °C, warmed up to 20 °C within 1 h; poured into 5 percent HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapn., recrystn. from hot toluene, elem. anal.;

1: diethyl malonate With sodium methylate T=20 - 60°C; Industry scale; 2: 1-bromo-2,4,6-trifluoro-benzene With copper(I) bromide in ethanol T=75 - 100°C; P=760.051 Torr; 12.3333 h; Industry scale; Product distribution / selectivity;

hydrogenchloride; copper monobromide