Reaction #68408

Reaction equation

1-iodo-4-methoxy-2-nitrobenzene

3-methyl-1-butyne

→

title compound

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

Solvents

Et3N

DMF

Conditions

Workup

1. 1
   Concentrationwas concentrated
2. 2
   workup.ADDITIONThe resulting mixture was diluted with EtOAc
3. 3
   Washwashed with H2O, brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

Procedure

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.

Source