2-Naphthalenecarboxylic acid, 1-bromo-, methyl ester → HCID 68846043, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1Br)=[O:4]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:11]=[CH:10][CH2:9][CH2:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:5][CH:6]=1)=[O:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
530 mg g 1-bromo-naphthalene-2-carboxylic acid methyl ester and 9 mg tris(dibenzylideneacetone)dipalladium(0) were placed in a reaction vial, which was evacuated and backfilled with argon three times. Via septum 125 μl tri-tert.butylphosphine (10% in hexane), 291 mg 4-phenyl-1-butene, 470 μl N,N-dicyclohexylmethylamine and 1.8 ml dioxane were added. After 2 h at 80° C., the reaction mixture was cooled and filtrated over silica with diethyl ether. After concentration of the organic phase the resulting residue was purified by chromatography on silica (ethyl acetate/heptane) to yield 175 mg of a mixture of the (E)- and (Z)-isomers of 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid methyl ester.