1: N-bromosuccinmide; ammonium acetate / 2,2-dimethyl-1-propanenitrile / Reflux 2: sodium hydroxide / anhydrous N,N-diethylformamide / 2 h / 110 °C View Scheme

cerium(III) chloride in tetrahydrofuran T=20°C;

1: 74 percent / anhydrous cerium(III) chloride / tetrahydrofuran / 20 °C 2: 37 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr View Scheme

1.1: 74 percent / anhydrous cerium(III) chloride / tetrahydrofuran / 20 °C 2.1: 37 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr 3.1: methyl magnesium chloride / tetrahydrofuran / 2 h / Heating 3.2: 76 percent / tetrahydrofuran / Heating View Scheme

1.1: 74 percent / anhydrous cerium(III) chloride / tetrahydrofuran / 20 °C 2.1: 37 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr 3.1: methyl magnesium chloride / tetrahydrofuran / 2 h / Heating 3.2: 76 percent / tetrahydrofuran / Heating 4.1: 80 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating View Scheme