Potassium Iodide → 1-Cyclopentyl-3-iodobenzene

Temperature

70 °C

A solution of sodium nitrite (558 mg, 8.1 mmol) in water (10 ml) was added over 5 minutes to a cooled (5° C.) solution of 3-cyclopentyl-aniline hydrochloride (1 g, 5.1 mmol) in 6N HCl (25 ml). After 50 minutes, a solution of potassium iodide (2.02 g, 12.2 mmol) in water (10 ml) was added over 5 minutes. The mixture was then heated for 1 h at 70° C. After cooling down to room temperature, the pH was set over 11 with 6N NaOH, and the mixture was extracted three times with CH2Cl2 (3×100 ml). The combined organic layers were washed with sodium thiosulfate (75 ml) then brine (75 ml) and dried over MgSO4. The solvent was removed under reduced pressure to give 1.23 g of crude material (HPLC: 67%) which was purified by chromatography over silica gel (eluent:cyclohexane) to yield the above titled compound as an oil: 825 mg, yield: 60%.

1. temperatureAfter cooling down to room temperature
2. extractionthe mixture was extracted three times with CH2Cl2 (3×100 ml)
3. washThe combined organic layers were washed with sodium thiosulfate (75 ml)
4. dry with materialbrine (75 ml) and dried over MgSO4
5. customThe solvent was removed under reduced pressure
6. customto give 1.23 g of crude material (HPLC: 67%) which
7. customwas purified by chromatography over silica gel (eluent:cyclohexane)

ORD record

ord-7b212281e1ab43318e94b1915f67d573

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589095B2