Potassium Iodide → 1-Cyclopentyl-3-iodobenzene

Participants

Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence