potassium carbonate in N,N-dimethyl-formamide; acetone T=20°C; 5.5 h;

1: 2.3-difluoroanisole With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran T=-55°C; 2.5 h; 2: (4-morpholinyl)methanone in tetrahydrofuran T=-55°C; 1 h;

titanium tetrachloride in dichloromethane T=20°C;

1: 2.3-difluoroanisole With titanium tetrachloride in dichloromethane T=0°C; 0.0833333 h; 2: dichloromethoxy methane in dichloromethane T=20°C; Friedel-Crafts formylation; 0.5 h;

1.1: 78 percent / K2CO3 / dimethylsulfoxide / 0.5 h / 20 °C 2.1: TiCl4 / CH2Cl2 / 0.08 h / 0 °C 2.2: 71 percent / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / |Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: borane-THF / tetrahydrofuran / 24 h / 0 - 20 °C / |Inert atmosphere 2.2: 6 h / 60 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 4.1: potassium carbonate / N,N-dimethyl-formamide; acetone / 5.5 h / 20 °C View Scheme

1.1: borane-THF / tetrahydrofuran / 24 h / 0 - 20 °C / |Inert atmosphere 1.2: 6 h / 60 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide; acetone / 5.5 h / 20 °C View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide; acetone / 5.5 h / 20 °C View Scheme

boron tribromide in dichloromethane T=20°C;