3-Methylbut-1-yne → 4-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

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.

1. concentrationwas concentrated
2. additionThe resulting mixture was diluted with EtOAc
3. washwashed with H2O, brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

ORD record

ord-b7a226b1c835495eaf8a21b6a00f0eb4

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524917B2