Reacción #68408

Ecuación de reacción

1-iodo-4-methoxy-2-nitrobenzene

3-methyl-1-butyne

→

title compound

4-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

Disolventes

Et3N

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated
2. 2
   workup.ADDITIONThe resulting mixture was diluted with EtOAc
3. 3
   Lavadowashed with H2O, brine
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

Procedimiento

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (Aldrich, 10 g, 35.8 mmol) in Et3N (60 ml) and DMF (6 ml) was added CuI (34 mg, 0.18 mmol), Pd(PPh3)2Cl2 (126 mg, 0.18 mmol), and 3-methyl-1-butyne (5.0 ml, 73.5 mmol). The mixture was stirred at room temperature for 16 h and was concentrated. The resulting mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes) to yield the title compound as a brown oil.

Fuente