1-Chloro-4-iodobenzene → HCID 18407038, compound

A mixture of 1-chloro-4-iodobenzene (56 g, 235 mmol), dichlorobis(triphenylphosphine)palladium (II) (6.9 g, 9.8 mmol) and copper (I) iodide (1.9 g, 9.8 mmol) in diethylamine (200 mL) was degassed with bubbling nitrogen. Methyl 4-pentynoate (Description 1, 22.0 g, 196 mmol) was added dropwise and the mixture was degassed with bubbling nitrogen. The mixture was heated under reflux for 24 h., cooled and poured into saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate and the combined organic fractions were washed with saturated aqueous ammonium chloride. The solvent was evaporated under reduced pressure and the residue was triturated with hexane. The mixture was filtered, dried (MgSO4) and concentrated under reduced pressure. The mixture was refrigerated and the solid was collected and dried in vacuo to give the title compound as pale brown solid (21.0 g, 48%). 1H NMR (360 MHz, CDCl3) δ 7.31 (2H, d, J 7.5 Hz), 7.25 (2H, d, J 7.5 Hz), 3.72 (3H, s), 2.73 (2H, t, J 7.3 Hz), and 2.62 (2H, t, J 7.3 Hz).

1. customwas degassed with bubbling nitrogen
2. customthe mixture was degassed with bubbling nitrogen
3. temperatureThe mixture was heated
4. temperatureunder reflux for 24 h.
5. temperaturecooled
6. additionpoured into saturated aqueous ammonium chloride
7. extractionThe mixture was extracted with ethyl acetate
8. washthe combined organic fractions were washed with saturated aqueous ammonium chloride
9. customThe solvent was evaporated under reduced pressure
10. customthe residue was triturated with hexane
11. filtrationThe mixture was filtered
12. dry with materialdried (MgSO4)
13. concentrationconcentrated under reduced pressure
14. customthe solid was collected
15. customdried in vacuo

ORD record

ord-4469a09d8035400a95f09c7269d0847d

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06476045B2