N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → [2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

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Reaction Conditions

Reaction Steps

A mixture of N,N-dimethylformamide diisopropyl acetal (1.32 mL, 6.31 mmol) and 1-bromo-2-fluoro-4-methyl-5-nitro-benzene (1.23 g, 5.26 mmol) in dry DMF (15.0 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-bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as dark red solid (1.89 mg, 83%). 1H NMR (CDCl3, 400 MHz): 2.92 (s, 6H), 5.88 (d, J=12.3 Hz, 1H), 6.98 (d, J=13.2 Hz, 1H), 7.11 (d, J=10.8 Hz, 1H), 8.10 (d, J=6.9 Hz, 1H).

Provenance & Evidence