Iodine → HCID 18437784, compound

Temperature

-78 °C

To a solution of 1-butyl-4-phenylimidazole (4.0 g, 20 mmol) in 60 ml of anhydrous THF at −78° C. under nitrogen is added a solution of n-butyllithium in hexane (1.6M, 13.13 ml, 21 mmol, 1.05 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 h followed by dropwise addition of a solution of iodine (5.33 g, 21 mmol, 1.05 eq.) in 40 ml of THF. The resulting solution is stirred at −78° C. for 30 min. and then warmed to room temperature. Saturated ammonium chloride (30 mL) is added to quench the reaction. The resulting mixture is evaporated a reduced pressure to remove THF, extracted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and evaporated. Purification by silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 5:1) affords 5.73 g of 1-butyl-2-iodo-4-phenylimidazole. 1H NMR (400 MHz, CDCl3) δ 7.73 (2H, dd, J=1.2, 8.4 Hz), 7.36 (2H, m), 7.30 (1H, s), 7.24 (1H, m), 3.92 (2H, t, J=7.2 Hz), 1.79 (2H, m), 1.41 (2H, m), 0.98 (3H, t, J=7.2 Hz); MS (+VE) m/z 327 (M+1).

1. stirringThe resulting solution is stirred at −78° C. for 30 min.
2. temperaturewarmed to room temperature
3. customto quench
4. customthe reaction
5. customThe resulting mixture is evaporated a reduced pressure
6. customto remove THF
7. extractionextracted with ethyl acetate
8. washwashed with water and brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated
12. customPurification by silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 5:1)

ORD record

ord-1dad2f52ec5a4c6cb4c1011bd7ec4b22

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07186734B2