water; toluene-4-sulfonic acid in methanol 24 h; Ambient temperature; Yield given;

1: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 2: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 3: TsOH, H2O / methanol / 24 h / Ambient temperature View Scheme

1: 89 percent / TsOH / 24 h / Ambient temperature 2: 93 percent / diisobutylaluminum hydride (DIBAH) / diethyl ether; toluene / 2 h / -20 °C 3: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 4: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 5: TsOH, H2O / methanol / 24 h / Ambient temperature View Scheme

1: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 2: TsOH, H2O / methanol / 24 h / Ambient temperature View Scheme

1: 93 percent / diisobutylaluminum hydride (DIBAH) / diethyl ether; toluene / 2 h / -20 °C 2: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 3: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 4: TsOH, H2O / methanol / 24 h / Ambient temperature View Scheme

1: NaI / acetone 2: Cl2CHCO2H 3: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme

1: Py 2: (i) Li, CuI, Et2O, (ii) /BRN= 2361172/ 3: KF / dimethylformamide; H2O 4: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme

1: (i) Li, CuI, Et2O, (ii) /BRN= 2361172/ 2: KF / dimethylformamide; H2O 3: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme

1: KF / dimethylformamide; H2O 2: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme

1: Cl2CHCO2H 2: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme