1-Iodo-4-octylbenzene → HCID 86660604, compound

Temperature

0 °C

To a solution of the product of Step A (0.32 g; 1.01 mmol) in anhydrous THF (2 ml) 2 M iPrMgCl in THF (0.56 ml; 1.11 mmol) was added at −15° C. under N2, followed 1.27 M solution of anhydrous ZnCl2 in THF (0.41 ml; 0.52 mmol), after stirring for 1 h at 0° C. The resulting mixture was stirred for 30 min on ice-bath under N2 and the solution of the product of Step B (0.16 g; 0.51 mmol) and CuCl2 (2.5 mol %) in anhydrous THF (10 ml) was added. The resulting mixture was allowed to warm up to room temperature and stirred for additional 10 min. This was diluted to 20 ml with Et2O and washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9:1) to give the title compound (0.06 g; 31%), as a creamy syrup. 1H-NMR (CDCl3) 7.07 (d, 2H, J=8.6 Hz); 6.84 (d, 2H, J=8.6 Hz); 3.55 (t, 4H, J=5 Hz); 3.06 (t, 4H, J=5 Hz); 2.51 (t, 2H, J=7.94 Hz); 1.55-1.38 (m, 11H); 1.26 (m, 10H); 0.86 (t, 3H, J=6.93 Hz).

1. stirringThe resulting mixture was stirred for 30 min on ice-bath under N2
2. temperatureto warm up to room temperature
3. stirringstirred for additional 10 min
4. washwashed with 5% NaHCO3, H2O, brine
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. customThe filtrate was evaporated under reduced pressure
8. customthe residue was purified by FCC (SiO2, hexane/EtOAc 9:1)

ORD record

ord-20265569501a4cb1a853190856a751ca

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592399B2