ethyl mercaptan sodium salt in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=170 - 180°C;

1: 96.4 percent / H2 / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min 3: 24.6 percent / EtSNa / hexamethylphosphoric acid triamide / 170 - 180 °C View Scheme

toluene-4-sulfonic acid in benzene T=20°C; 0.333333 h;

1: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min 2: 24.6 percent / EtSNa / hexamethylphosphoric acid triamide / 170 - 180 °C View Scheme

1: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min 2: 24.6 percent / EtSNa / hexamethylphosphoric acid triamide / 170 - 180 °C View Scheme

1: 71 percent / BBr3 / CH2Cl2 / 1.) -70 deg C, 2.) room temp., 2 h 2: 15 percent / toluene-p-sulphonic acid / benzene / 0.33 h / 20 °C View Scheme