1: 2-iodo-4-tert-butylaniline With hydrogenchloride; sodium nitrite in tetrahydrofuran; diethyl ether; acetonitrile T=-5 - 0°C; 1.5 h; 2: diethylamine With potassium carbonate in tetrahydrofuran; diethyl ether; acetonitrile 1.5 h; Further stages.;

1.1: 90 percent / (BnEt3N)ICl2; CaCO3 / CH2Cl2; methanol / 3 h / 20 °C 2.1: aq. HCl; NaNO2 / diethyl ether; tetrahydrofuran; acetonitrile / 1.5 h / -5 - 0 °C 2.2: 92 percent / aq. K2CO3 / acetonitrile; diethyl ether; tetrahydrofuran / 1.5 h View Scheme

1: 93 percent / Et3N / PdCl2(PPh3)2; CuI / 60 °C 2: 82 percent / iodomethane / 24 h / 120 °C View Scheme