1-Bromo-4-iodobenzene → 1-Bromo-4-(1-propynyl)benzene

Into a 250-mL three neck round-bottom flask, which was maintained with an inert atmosphere of nitrogen, was placed 1-bromo-4-iodobenzene (2.00 g, 7.07 mmol), PdCl2(PPh3)2 (99.2 mg, 0.14 mmol), CuI (26.8 mg, 0.14 mmol), trimethyl(prop-1-yn-1-yl)silane (2.08 mL, 14.1 mmol) and tetrahydrofuran/TEA (9:1) (100 mL). Stirring was initiated and tetrabutylammonium fluoride (3.69 g, 14.1 mmol) was added rapidly to the mixture. The resulting mixture was stirred for 18 h at room temperature, then concentrated under reduced pressure. The residue diluted with water (100 mL) and extracted with ethyl acetate (3×50 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield the title compound as a light yellow oil (1.0 g, 73%).

1. stirringThe resulting mixture was stirred for 18 h at room temperature
2. concentrationconcentrated under reduced pressure
3. additionThe residue diluted with water (100 mL)
4. extractionextracted with ethyl acetate (3×50 mL)
5. dry with materialThe organic extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography with petroleum ether as the eluent

ORD record

ord-75dbb2eb72914f9e9c2b752e02814bac

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2