1: TsOH*H2O / methanol / Heating 2: PBr3, Py / diethyl ether 3: (i) EtMgBr, (ii) CuCl, (iii) /BRN= 1815813/ 4: PBr3, Py / diethyl ether 5: (i) EtMgBr, Et2O, (ii) /BRN= 1816937/, CuCl 6: H2 / Lindlar catalyst / petroleum ether 7: (i) EtMgBr, Et2O, (ii) /BRN= 1900390/, Et2O View Scheme

toluene-4-sulfonic acid in methanol Heating;

1: 92 percent / dimethylsulfoxide / 20 h / 80 °C 2: 85 percent / 10percent aq. NaOH / methanol / Heating 3: 82 percent / p-toluenesulfonic acid / methanol / 20 h 4: 53 percent / I2, (4-dimethylaminophenyl)diphenylphosphine / diethyl ether / 0.25 h / 0 °C View Scheme

1: TsOH*H2O / methanol / Heating 2: PBr3, Py / diethyl ether 3: (i) EtMgBr, (ii) CuCl, (iii) /BRN= 1815813/ 4: PBr3, Py / diethyl ether 5: (i) EtMgBr, Et2O, (ii) /BRN= 1816937/, CuCl 6: H2 / Lindlar catalyst / petroleum ether 7: (i) EtMgBr, Et2O, (ii) /BRN= 1900390/, Et2O, (iii) /BRN= 102415/, Et2O View Scheme

1: H2, quinoline / 5 percent palladium on calcium carbonate / methanol / Ambient temperature 2: p-toluenesulphonic acid / methanol / 2 h / Heating 3: 1.) propionic acid / 1.) 130 deg C, 3 h, 2.) 145 deg C, 14 h 4: 90 percent / ozone / methanol / 1 h / -30 deg C to -60 deg C View Scheme

in methanol; dimethyl sulfoxide

1.1: dimethylsulfoxide / Heating 2.1: sodium hydroxide / methanol / 20 h / Heating 3.1: 6.3 g / BF3 / 4 h / 20 °C 4.1: hydrogen / Lindlar's catalyst / 0 °C 5.1: tetrabromomethane; triphenyl phosphine 6.1: 5.1 g / sodium hydride 7.1: sodium hydride / tetrahydrofuran / 2 h / -5 °C 7.2: 74 percent / tetrahydrofuran; various solvent(s) / -78 - -25 °C View Scheme

1: TsOH*H2O / methanol / Heating 2: PBr3, Py / diethyl ether View Scheme

1: 80 percent / dimethylsulfoxide / 50 h / 40 - 45 °C 2: 86 percent / H2O 3: 95 percent / diethyl ether / 12 h / Ambient temperature View Scheme

1: 92 percent / dimethylsulfoxide / 20 h / 80 °C 2: 84 percent / p-toluenesulfonic acid / methanol / Ambient temperature 3: 82 percent / PBr3 / diethyl ether View Scheme