Reaction #1563869

Reaction equation

pyridine

4-Bromo-1H-imidazole

phenylboronic acid

→

4-bromo-1-phenyl-1H-imidazole

Yield 26.4%

Solvents

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe reaction mass was then filtered through Celite
2. 2
   Washwashed with methanol
3. 3
   Concentrationconcentrated
4. 4
   Otherpurified by silica gel chromatography (eluent 15% ethyl acetate/hexane)

Procedure

4-Bromo-1H-imidazole (500 mg, 3.4 mmol, 1 eq), phenylboronic acid (830 mg, 6.8 mmol, 2 eq), anhydrous cupric acetate (926 mg, 5.1 mmol), activated 4 Å molecular sieves (2 g) and pyridine (0.3 ml) were combined in dichloromethane (20 ml) and stirred for 2 days in the presence of air. The reaction mass was then filtered through Celite, washed with methanol, and concentrated and purified by silica gel chromatography (eluent 15% ethyl acetate/hexane) to afforded yellowish sticky solid 4-bromo-1-phenyl-1H-imidazole (200 mg, 26%).

Source