phenyltrimethylammonium tribromide in tetrahydrofuran T=28°C; 27 h;

Nafion-TMS in chloroform 21 h; Heating;

toluene-4-sulfonic acid in chloroform Heating;

toluene-4-sulfonic acid; benzene

bromine 1.) 0 deg C, 2.) methanol, electrolysis, 2.5 F/mol; Yield given. Multistep reaction;

1: 80 percent / potassium tert-butoxide / dimethylsulfoxide 2: 1.) aq. mercuric acetate, 2.) aq. sodium hydroxide, sodium borohydride / 1.) THF, 30 deg C, 3 h, 2.) 0 deg C, 1 h 3: 86 percent / chromium trioxide-pyridine / CH2Cl2 4: 93 percent / 25percent sulphuric acid, silica gel / CH2Cl2 / 6 h / Ambient temperature View Scheme

1: NaOH / methanol / 40 h / Heating 2: 55 percent / 5percent aq. H2SO4 / 0.5 h / Ambient temperature View Scheme

potassium tert-butylate in dimethyl sulfoxide

1: 80 percent / potassium tert-butoxide / dimethylsulfoxide 2: 1.) aq. mercuric acetate, 2.) aq. sodium hydroxide, sodium borohydride / 1.) THF, 30 deg C, 3 h, 2.) 0 deg C, 1 h View Scheme

1: 80 percent / potassium tert-butoxide / dimethylsulfoxide 2: 1.) aq. mercuric acetate, 2.) aq. sodium hydroxide, sodium borohydride / 1.) THF, 30 deg C, 3 h, 2.) 0 deg C, 1 h 3: 86 percent / chromium trioxide-pyridine / CH2Cl2 View Scheme