bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane T=50°C; metathesis; P=7500.6 Torr; 2 h;

sulfuric acid Heating;

1.1: magnesium / tetrahydrofuran / 2 h / 45 °C 1.2: 82 percent / CuCl / tetrahydrofuran / 1 h / 0 °C 2.1: 98 percent / H2SO4 / Heating View Scheme

1: 75 percent / HBr, HOAc / a) r.t., 16 h, b) 100 deg C, 4 h 2: 90 percent / NaI / acetone / 16 h / Heating 3: 89 percent / 4 h / Ambient temperature View Scheme

1: 90 percent / NaI / acetone / 16 h / Heating 2: 89 percent / 4 h / Ambient temperature View Scheme

1: 89 percent / 4 h / Ambient temperature View Scheme

Yield given. Multistep reaction. Title compound not separated from byproducts;

1: 13-tetradecenoic acid methyl ester With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; 4 h; 2: (4-bromophenyl)(4-methylphenyl)methanone With triphenyl-arsane; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran; water; N,N-dimethyl-formamide Suzuki coupling; Heating;

bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane olefin metathesis; Heating;

1: 87 percent / Grubbs catalyst I / CH2Cl2 / Heating 2: 99 percent / H2 / Pd/C / hexane / 20 °C 3: 99 percent / AlCl3 / CH2Cl2 / 20 °C View Scheme