Reaction #92932

Reaction equation

1-bromo-2-(4-ethylphenyl)-2-oxoethane

1-methylimidazole

→

1-methyl-3-[2-(4-ethylphenyl)-2-oxoethyl]-1H-imidazolium bromide

Yield 38.2%

Solvents

diethyl ether

Conditions

Workup

1. 1
   OtherThe reaction solvent was decanted
2. 2
   Washthe residue was washed with diethyl ether
3. 3
   workup.DISSOLUTIONdissolved in a small amount of acetonitrile
4. 4
   workup.ADDITIONThe resulting solution was diluted with a small amount of ethyl acetate, whereupon a brown precipitate
5. 5
   Otherformed
6. 6
   OtherThe solid was collected
7. 7
   Otherrecrystallized from acetonitrile/ethyl acetate

Procedure

A solution of 4.41 g (0.019 mol) of 1-bromo-2-(4-ethylphenyl)-2-oxoethane and 1.65 g (0.02 mol) of 1-methylimidazole in 40 ml of diethyl ether was stirred at room temperature for approximately 18 hours. The reaction solvent was decanted, and the residue was washed with diethyl ether and dissolved in a small amount of acetonitrile. The resulting solution was diluted with a small amount of ethyl acetate, whereupon a brown precipitate formed. The solid was collected and recrystallized from acetonitrile/ethyl acetate to provide 2.26 g of 1-methyl-3-[2-(4-ethylphenyl)-2-oxoethyl]-1H-imidazolium bromide as fine yellow brown needles. (38% yield) mp=177°-179° C.

Source