Dimethylformamide dimethyl acetal → [2-(4-Iodo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

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Reaction Conditions

Reaction Steps

A mixture of N,N-dimethylformamide dimethyl acetal (0.30 mL, 2.31 mmol) and 1-iodo-2-fluoro-4-methyl-5-nitro-benzene (0.50 g, 1.78 mmol) in dry DMF (3.0 mL) was stirred at 125° C. for 3 h. The resulting mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was washed with hexane to give [2-(4-iodo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as dark red solid (0.37 mg, 62%). 1H NMR (CDCl3, 400 MHz): 2.97 (s, 6H), 5.92 (d, J=13.3 Hz, 1H), 7.02 (d, J=13.3 Hz, 1H), 7.09 (d, J=10.2 Hz, 1H), 8.30 (d, J=6.2 Hz, 1H). 13C NMR (CDCl3, 100 MHz,): 40.8, 108.9, 109.1, 137.0, 139.3, 146.0.

Provenance & Evidence