4-Iodoaniline → 4-[(4-Hexylphenyl)ethynyl]aniline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-iodoaniline (10.0 g, 45.6 mmol, Aldrich) and 1-eth-1-ynyl-4-hexylbenzene (10.0 g, 53.0 mol, Maybridge) in anhydrous acetonitrile (200 mL) under nitrogen was added CuI (0.43 g, 2.2 mmol), TEA (14.0 g, 138 mmol) followed by Pd(PPh3)2Cl2 (1.6 g, 2.2 mmol). The reaction mixture was stirred at 85° C. for 22 hours. The solvent was removed under reduced pressure. The residue was diluted with Et2O (200 mL) 20 and washed with water and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by chromatography Wet ether/EtOAc 4/1) to give 11.0 g (87%) of the title compound as a pale yellow solid. TLC-Pet ether/EtOAc (4/1): Rf=0.4. HPLC purity >98%.

Provenance & Evidence