2,5-Dichloroaniline → HCID 178512050, compound

Participants

Reaction Steps

Under N2 atmosphere, to a solution of 2,5-dichloroaniline (341 mg, 2.1 mmol) in 2 mL dry THF was added sodium bis(trimethylsilyl)amide (2.1 mL, 1M solution in THF, 2.1 mmol). After the mixture was stirred at ambient temperature for 40 min, a solution of 5-bromo-thiophene-2-carbonitrile (376 mg, 2 mmol) in 2 mL dry THF was added dropwise. The reaction mixture was stirred overnight, and then poured into 100 mL ice water. The orange precipitate was collected by filtration, washed with a solution of ether and hexane (3/7, v/v), and air dried to give a light orange solid (653 mg, 94% yield). 1H-NMR (400 MHz, MeOH-d4): δ 6.94 (d, 1H), 6.99 (dd, 1H), 7.06 (d, 1H), 7.32 (d, 1H), 7.37 (d, 1H).

Provenance & Evidence