sodium hydroxide in ethanol T=20°C; 3 h;

indium; triphenylphosphine; lithium chloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in N,N-dimethyl-formamide T=100°C; 1 h;

1: bromobenzoic acid ethyl ester With diisobutylaluminium hydride; magnesium; lithium chloride; zinc(II) chloride in tetrahydrofuran T=25°C; 3 h; 2: allyl bromide With copper (I) cyanide; lithium chloride in tetrahydrofuran T=25°C; 0.5 h;

indium(III) chloride; indium; lithium chloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in N,N-dimethyl-formamide T=100°C; 2 h;

1: 2-Iodo-benzoic acid ethyl ester With chloro-trimethyl-silane; aluminium; lithium chloride; PbCl2 in tetrahydrofuran T=25 - 50°C; Inert atmosphere; 2: With zinc diacetate in tetrahydrofuran T=25°C; 0.333333 h; Inert atmosphere; 3: allyl bromide With CuCN*2LiCl in tetrahydrofuran T=0°C; 1 h; Inert atmosphere; chemoselective reaction;

1.1: thionyl chloride / 4 h / 60 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / -40 °C 2.2: CuCN; LiCl / tetrahydrofuran 2.3: 78 percent / tetrahydrofuran View Scheme