1: 2-fluoro-3-methyl-4-aminophenyl iodide With (4-Methylphenyl)-magnesium bromide in tetrahydrofuran 2: With isopropylmagnesium chloride in tetrahydrofuran 3: carbon dioxide in tetrahydrofuran

1.1: (4-Methylphenyl)-magnesium bromide / tetrahydrofuran 2.1: SPB; potassium iodide / water; acetic acid / 1.5 h / 5 - 20 °C 2.2: 1 h / 0 - 10 °C 3.1: (4-Methylphenyl)-magnesium bromide / tetrahydrofuran / 0.5 h / -10 - 0 °C 3.2: 0.5 h / -10 - 0 °C 3.3: 1 h / -10 - 15 °C View Scheme

1.1: (4-Methylphenyl)-magnesium bromide / tetrahydrofuran 2.1: SPB; potassium iodide / water; acetic acid / 1.5 h / 5 - 20 °C 2.2: 1.5 h / 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 8 h / 60 °C / 760.05 Torr View Scheme

1.1: (4-Methylphenyl)-magnesium bromide / tetrahydrofuran 2.1: SPB; potassium iodide / water; acetic acid / 1.5 h / 5 - 20 °C 2.2: 1 h / 0 - 10 °C 3.1: (4-Methylphenyl)-magnesium bromide / tetrahydrofuran / 0.5 h / -10 - 0 °C 3.2: 0.5 h / -10 - 0 °C 3.3: 0.33 h / -10 - 15 °C 4.1: water; sodium hydroxide / 8 h / 80 °C View Scheme

1: 2-fluoro-3-methyl-4-aminophenyl iodide With (4-Methylphenyl)-magnesium bromide in tetrahydrofuran 2: With isopropylmagnesium chloride in tetrahydrofuran 3: carbon dioxide in tetrahydrofuran