n-butyllithium in tetrahydrofuran T=-80°C; 0.166667 h;

1: 1.) n-BuLi / 1.) THF, -78 degC, 90 min; 2.) THF, -78 degC, 15 min 2: 75 percent / CuSO4 / Ambient temperature View Scheme

1.1: t-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 1.2: n-Bu3SnCl; HCl / diethyl ether; hexane / 3.5 h / -78 - 20 °C 1.3: 931 mg / PdCl2(PhCN)2; Ph3As; CuI / 1-methyl-pyrrolidin-2-one / 80 °C 2.1: 74 percent / CO; dppp; 1,10-phenanthroline monohydrate / Pd(dba)2 / dimethylformamide / 24 h / 80 °C / 4560 Torr View Scheme

n-butyllithium 1.) THF, -78 degC, 90 min; 2.) THF, -78 degC, 15 min; Yield given. Multistep reaction;

1: 90 percent / n-BuLi / tetrahydrofuran / 0.17 h / -80 °C 2: 75 percent / n-BuLi / tetrahydrofuran / 1 h / 0 °C View Scheme

toluene-4-sulfonic acid in benzene 24 h; Heating;

1: 76 percent / Br2, Et3N / CCl4 / 1.) 0 deg C, 5 min, 2.) RT, 2 h 2: 87 percent / TsOH / benzene / 62 h / Heating; azeotropic removal of water View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.333333 h;