1: N-(4-bromo-2-iodo-6-methylphenyl)-2-methyl-(2E)-butenamide With sodium hydride in tetrahydrofuran T=0°C; 0.25 h; 2: methyl iodide in tetrahydrofuran 1 h;

1.1: trimethylaluminum / hexane; benzene / 1 h / 0 - 20 °C 1.2: 90 percent / hexane; benzene / 6 h / 80 °C 2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 2.2: 98 percent / tetrahydrofuran / 1 h View Scheme

1.1: trimethylaluminum / hexane; benzene / 1 h / 0 - 20 °C 1.2: 90 percent / hexane; benzene / 6 h / 80 °C 2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 2.2: 98 percent / tetrahydrofuran / 1 h View Scheme

1.1: 67 percent / iodine; silver sulfate / ethanol / 3 h 2.1: trimethylaluminum / hexane; benzene / 1 h / 0 - 20 °C 2.2: 90 percent / hexane; benzene / 6 h / 80 °C 3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 3.2: 98 percent / tetrahydrofuran / 1 h View Scheme