1: propanedioic acid monoethyl ester With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2: 4-bromo-2-fluoro-3-methoxybenzoic acid chloride in tetrahydrofuran; hexane; dichloromethane T=-78 - 10°C;

1.1: potassium carbonate / dimethylformamide / 6 h / 80 °C 2.1: H2 / Pd/C / methanol / 27 h / 20 °C 3.1: aq. HBr; NaNO2 / 0 - 5 °C 3.2: CuBr; aq. HBr / 60 °C 4.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 4.2: tetrahydrofuran; hexane / -78 - 20 °C 5.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 6.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 6.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1.1: H2 / Pd/C / methanol / 27 h / 20 °C 2.1: aq. HBr; NaNO2 / 0 - 5 °C 2.2: CuBr; aq. HBr / 60 °C 3.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 3.2: tetrahydrofuran; hexane / -78 - 20 °C 4.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 5.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 5.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: tetrahydrofuran; hexane / -78 - 20 °C 2.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 3.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 3.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 2.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1.1: aq. HBr; NaNO2 / 0 - 5 °C 1.2: CuBr; aq. HBr / 60 °C 2.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: tetrahydrofuran; hexane / -78 - 20 °C 3.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 4.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 4.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme