Dimethylformamide → 3-Iodoaniline

Participants

Reaction Conditions

Reaction Steps

Into 12 mL of dry DMF in an oven dried, nitrogen filled tube was placed M (3.0 g, 15 mmol), 1-iodo-3-bromobenzene (1.6 mL, 13 mmol), palladium(II)acetate (0.42 g, 1.9 mmol), tetrabutylammoniumchloride (3.5 g, 13 mmol), and solid NaHCO3 (2.6 g, 31 mmol). The tube was sealed and heated to 80° C. for 16 hours. The cooled reaction mixture was diluted with EtOAc, passed through a small plug of silica gel to remove the catalyst, and extracted 2× with brine. The solution was then dried over Na2SO4, concentrated, and purified by flash chromatography eluting with 2:1 and 1:1 heptane: EtOAc to afford N (1.8 g, 5 mmol, 40%) (MS;M+H: 356.1, 358.1). Likewise N′ was formed (0.92 g, 3.1 mmol, 77%) (MS;M+H: 293.2) from M (1.0 g, 5 mmol), 3-iodoaniline (0.5 mL, 4.2 mmol), Pd(OAc)2 (0.14 g, 0.62 mmol), Bu4NCl (1.16 g, 4.2 mmol), and NaHCO3 (0.87 g, 10 mmol) in 4 mL of dry DMF.

Provenance & Evidence