Benzene, 1-bromo-3-nitro- → HCID 86641448, compound

Participants

Reaction Conditions

Reaction Steps

2,2,2-Trifluoro-N-(prop-2-ynyl)acetamide (3.4 g, 22.2 mmol), 1-bromo-3-nitrobenzene (14) (3.0 g, 14.85 mmol), Pd(Ph3P)4 (0.85 g, 0.74 mmol) and CuI (0.14 g, 0.74 mmol) was added to triethylamine (30 mL) and the mixture was flushed with argon for 15 min. The reaction mixture was stirred at 90° C. for 16 h, cooled and diluted with ethyl acetate. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 15% to 20% EtOAc in hexane) gave 2,2,2-trifluoro-N-(3-(3-nitrophenyl)prop-2-ynyl)acetamide as a brown semi-solid. Yield (1.95 g, 48%); 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 8.16 (d, J=8.0 Hz, 1H), 1.79 (d, J=7.6 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.34 (s, 1H), 4.38 (s, 2H).

Provenance & Evidence