1: With trichlorophosphate in acetonitrile T=80 - 83°C; Bischler-Napieralski reaction; 2 h; 2: With sodium tetrahydroborate in methanol T=-78°C; 2 h;

sodium tetrahydroborate in methanol Heating;

1.1: Br2 2.1: SOCl2 3.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 4.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 4.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1.1: SOCl2 2.1: 89.7 percent / aq. Na2CO3 / diethyl ether; benzene / 1 h / 0 - 5 °C 3.1: 86 percent / BF3*Et2O; BH3*THF / tetrahydrofuran / 2.5 h / 70 - 80 °C 4.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 5.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 5.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 2.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 2.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1.1: SOCl2 2.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 3.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 3.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1.1: 89.7 percent / aq. Na2CO3 / diethyl ether; benzene / 1 h / 0 - 5 °C 2.1: 86 percent / BF3*Et2O; BH3*THF / tetrahydrofuran / 2.5 h / 70 - 80 °C 3.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 4.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 4.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1.1: 86 percent / BF3*Et2O; BH3*THF / tetrahydrofuran / 2.5 h / 70 - 80 °C 2.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 3.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 3.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

hydrogenchloride; tin