1: With trichlorophosphate in toluene Vilsmeier-Haack reaction; Heating; 2: With sodium hydroxide in tetrahydrofuran T=20°C;

tetrabutyl-ammonium chloride; sodium acetate; tris-(o-tolyl)phosphine; palladium diacetate in N,N-dimethyl-formamide T=120°C; Heck reaction; 16 h; Product distribution; Further Variations:ReagentsTemperaturesmicrowave irradiation;

1: 63 percent / 120 °C 2: 99 percent / AcONa; tri(o-tolyl)phosphine; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 100 °C / Irradiation View Scheme

1.1: 83 percent / tetrabutylammonium sulfate; sodium hydroxide / benzene; H2O / 24 h / 40 °C 2.1: phosphorus oxychloride / toluene / Heating 2.2: 78 percent / sodium hydroxide / tetrahydrofuran / 20 °C View Scheme

1.1: 100 percent / 0.25 h / 200 °C 2.1: 83 percent / tetrabutylammonium sulfate; sodium hydroxide / benzene; H2O / 24 h / 40 °C 3.1: phosphorus oxychloride / toluene / Heating 3.2: 78 percent / sodium hydroxide / tetrahydrofuran / 20 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / -78 - 20 °C 1.2: 115 mg / lithium tetrachlorocuprate(II) / tetrahydrofuran; hexane / 13 h / 20 °C 2.1: 100 percent / 0.25 h / 200 °C 3.1: 83 percent / tetrabutylammonium sulfate; sodium hydroxide / benzene; H2O / 24 h / 40 °C 4.1: phosphorus oxychloride / toluene / Heating 4.2: 78 percent / sodium hydroxide / tetrahydrofuran / 20 °C View Scheme

1.1: 83 percent / DIBALH / CH2Cl2; toluene / 0.33 h / -40 °C 2.1: lithium bromide; methanesulfonyl chloride; triethylamine / tetrahydrofuran / 15 h / 0 °C 3.1: lithium diisopropylamide / tetrahydrofuran; hexane / -78 - 20 °C 3.2: 115 mg / lithium tetrachlorocuprate(II) / tetrahydrofuran; hexane / 13 h / 20 °C 4.1: 100 percent / 0.25 h / 200 °C 5.1: 83 percent / tetrabutylammonium sulfate; sodium hydroxide / benzene; H2O / 24 h / 40 °C 6.1: phosphorus oxychloride / toluene / Heating 6.2: 78 percent / sodium hydroxide / tetrahydrofuran / 20 °C View Scheme

in benzene 96 h; Irradiation;

1: 99 percent / p-toluenesulfonic acid monohydrate / toluene / Heating 2: 50 percent / benzene / 96 h / Irradiation View Scheme