Potassium Carbonate → 2,4-Dichloro-3-ethenylbenzenamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-3-iodoaniline (9.0 g, 31 mmol) in DME/water (180 mLU60 mL) is added vinyl triboroxine pyridine complex (5.0 g, 20.8 mmol) and K2CO3 (8.5 g, 62.0 mmol). The reaction mixture is stirred and N2 is bubbled in for 15 min. Tetrakis(triphenylphosphine) palladium(0) (1.8 g, 1.6 mmol) is added at room temperature and N2 is bubbled in for additional 20 min. The reaction mixture is heated to 80° C. and stirred for 18 hours, when the GC-MS showed the reaction is complete. The mixture is filtered and washed with ether (400 mL) and water (50 mL). The organic layer is separated and washed with brine and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-vinylaniline.

Provenance & Evidence