Hexachloroethane → 2-chloro-1-methyl-4-phenyl-1H-Imidazole

To a solution of 1-methyl-4-phenyl-1H-imidazole (0.600 g, 3.79 mmol) in 15 mL THF at −78° C. under nitrogen was added n-butyllithium 2.5 M in hexanes (1.67 ml, 4.17 mmol) dropwise over 3 min. The resulting orange-brown solution was allowed to stir for 30 min, at which time a solution of hexachloroethane (0.988 g, 4.17 mmol) in 5 mL THF was added slowly down the side of the flask. The orange-brown solution was allowed to stir for 1 h, and was quenched with sat'd aq. NH4Cl, warmed to ambient temperature, and stirred overnight. The mixture was extracted with EtOAc, the organic layers collected and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 2-chloro-1-methyl-4-phenyl-1H-imidazole as a brown solid. MS m/z=193 [M+H]+. Calc'd for C10H9N2Cl: 192.6.

1. additionwas added slowly down the side of the flask
2. customwas quenched with sat'd aq. NH4Cl
3. stirringstirred overnight
4. extractionThe mixture was extracted with EtOAc
5. customthe organic layers collected
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-7de132bffced40f69ba9eb35b93eac9d

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868177B2