Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(4-nitrophenyl)propiolate

Participants

Reaction Conditions

Reaction Steps

1-Iodo-4-nitrobenzene (550 mg, 2.17 mmol) in THF (4 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (552 mg, 298.6 mmol), CuI (30 mg, 0.16 mmol) and PdCl2(Ph3P)2 (14 mg, 0.020 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (506 mg, 2.03 mmol) in THF (2.5 mL) was added by syringe pump over a period of 6 h. After being cooled to room temperature, the mixture was filtered and washed with EtOAc. The filtrate was concentrated and purified by silica gel column chromatography to give the title compound 7-1 (551 mg, 74% yield) as a brown solid.

Provenance & Evidence