1,3-Propanediamine → 4-Iodobiphenyl

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 4-bromobiphenyl (234 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. 1,3-Propanediamine (8.4 μL, 0.10 mmol, 10 mol %) and n-pentanol (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 22 h. The resulting suspension was allowed to reach room temperature, diluted with 30% aq ammonia (2 mL), poured into water (20 mL), and extracted with dichloromethane (3×15 mL). The combined organic phases were dried (MgS04), concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide 269 mg (96% yield) of 4-iodobiphenyl as a white solid. Mp: 113-114° C. (lit. 112.5-113.5° C. See lbuki, E.; Ozasa, S.; Murai, K. Bull. Chem. Soc. Jpn. 1975, 48, 1868). The 1H and 13C spectra matched those reported in Dektar, J. L.; Hacker, N. P. J. Org. Chem. 1990, 55, 639.

Provenance & Evidence