in benzene T=80°C; Michaelis-Becker reaction; 8 h;

1: 4.2 g / Ph3P; Br2 / acetonitrile / 8 h / 80 °C 2: 49 percent / benzene / 8 h / 80 °C View Scheme

1: 13.2 g / MeONa / benzene / 15 h / 60 - 62 °C 2: 9.2 g / KOH / H2O / 4 h / Heating 3: 5.2 g / CuO / quinoline / Heating 4: 4.2 g / Ph3P; Br2 / acetonitrile / 8 h / 80 °C 5: 49 percent / benzene / 8 h / 80 °C View Scheme

1: 9.2 g / KOH / H2O / 4 h / Heating 2: 5.2 g / CuO / quinoline / Heating 3: 4.2 g / Ph3P; Br2 / acetonitrile / 8 h / 80 °C 4: 49 percent / benzene / 8 h / 80 °C View Scheme

1: 5.2 g / CuO / quinoline / Heating 2: 4.2 g / Ph3P; Br2 / acetonitrile / 8 h / 80 °C 3: 49 percent / benzene / 8 h / 80 °C View Scheme

1: N-bromosuccinimide; azobis(isobutyronitrile) / CCl4 / 1.5 h / Heating 2: 49 percent / benzene / 8 h / 80 °C View Scheme