1: With boron tribromide in dichloromethane T=-78°C; 5 h; 2: With triethanolamine in tetrahydrofuran; dichloromethane 15 h; Heating;

1.1: phosphorus oxychloride; DMF / Heating 2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / 60 °C 3.1: 100 percent / potassium carbonate / [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride / dimethylformamide; toluene; H2O / 15 h / 90 °C 4.1: BBr3 / CH2Cl2 / 5 h / -78 °C 4.2: triethanolamine / CH2Cl2; tetrahydrofuran / 15 h / Heating View Scheme

1.1: 83 percent / anisole; trifluoroacetic acid; trifluoromethanesulfonic acid / 1 h / 40 °C 2.1: phosphorus oxychloride; DMF / Heating 3.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / 60 °C 4.1: 100 percent / potassium carbonate / [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride / dimethylformamide; toluene; H2O / 15 h / 90 °C 5.1: BBr3 / CH2Cl2 / 5 h / -78 °C 5.2: triethanolamine / CH2Cl2; tetrahydrofuran / 15 h / Heating View Scheme

1.1: 100 percent / potassium carbonate / [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride / dimethylformamide; toluene; H2O / 15 h / 90 °C 2.1: BBr3 / CH2Cl2 / 5 h / -78 °C 2.2: triethanolamine / CH2Cl2; tetrahydrofuran / 15 h / Heating View Scheme