potassium tert-butylate in tetrahydrofuran T=-78 - 20°C; Wittig reaction;

1.1: 85 percent / Na2CO3 / Pd(PPh3)4 / dioxane; ethanol / 72 h / Heating 2.1: t-BuOK / tetrahydrofuran / 1 h / 20 °C 2.2: 75 percent / tetrahydrofuran / -78 - 20 °C View Scheme

1: 4-chloro-1-ethenylbenzene With magnesium in tetrahydrofuran 2: With zinc(II) chloride in tetrahydrofuran T=20°C; 3: 2,6-dibromo-4-methyl-benzenamine With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; tris-(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran Negishi coupling reaction; 12 h; Reflux;