Triethylamine → 4-Iodo-3-(naphthalen-2-yloxy)-benzoic acid methyl ester

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1B(O)O.[CH2:25](N(CC)CC)C>C(Cl)Cl>[CH3:25][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([I:11])=[C:2]([O:1][C:13]2[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[CH:3]=1

Komponenten

Versuchsvorschrift

A mixture of 3-hydroxy-4-iodo-benzoic acid acid methyl ester (0.505 g, 1.82 mmol), cupric acetate (0.330 g, 1.82 mmol), 2-naphthylboronic acid (0.625 g, 3.63 mmol) and powdered 4A molecular sieves (0.3 g) in CH2Cl2 (21 mL) was treated with triethylamine (1.27 mL, 9.08 mmol) and stirred at ambient temperature for 18 hr. The reaction mixture was filtered through celite, concentrated to dryness and chromatographed (SiO2, 5-40% EtOAc: hexane) to give the title compound. FAB mass spectrum (M+1) 405.