toluene-4-sulfonic acid in benzene

1: carbon dioxide; acetylene With (4,7-diphenyl-1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; caesium carbonate in N,N-dimethyl-formamide T=60°C; P=750.075 - 3750.38 Torr; 2 h; Autoclave; 2: 1-bromo-hexane in N,N-dimethyl-formamide T=60°C; 1 h; Autoclave; Concentration;

1: 85 percent / 48percent HBr / benzene / 28 h / Heating 2: 63 percent / DCC, DMAP / ethyl acetate / Ambient temperature 3: 97 percent / NaI / acetone / Ambient temperature 4: 1) Ph3SnH, AIBN, 2) KF / 1) benzene, 14 h, reflux, 2) water, ether, 1 h, r.t. View Scheme

1: 63 percent / DCC, DMAP / ethyl acetate / Ambient temperature 2: 97 percent / NaI / acetone / Ambient temperature 3: 1) Ph3SnH, AIBN, 2) KF / 1) benzene, 14 h, reflux, 2) water, ether, 1 h, r.t. View Scheme

1: 97 percent / NaI / acetone / Ambient temperature 2: 1) Ph3SnH, AIBN, 2) KF / 1) benzene, 14 h, reflux, 2) water, ether, 1 h, r.t. View Scheme

potassium fluoride; 2,2'-azo-bisisobutyronitrile; triphenylstannane 1) benzene, 14 h, reflux, 2) water, ether, 1 h, r.t.; Yield given. Multistep reaction;