Reaction #696711

Reaction equation

trichloroacetyl chloride

N-methylpyrrole

→

2-(trichloroacetyl)pyrrole

Yield 92.7%

Solvents

ethyl ether

ethyl ether

Conditions

Workup

1. 1
   Otherquenched by the dropwise addition of a solution of 400 g potassium carbonate in 1.5 liters water
2. 2
   OtherThe layers were separated
3. 3
   Concentrationthe ether layer concentrated in vacuo

Procedure

To a well stirred solution of trichloroacetyl chloride (1 kg, 5.5 mole) in 1.5 liter ethyl ether in a 12 liter flask was added dropwise over a period of 3 h a solution of N-methylpyrrole (0.45 kg, 5.5 mole) in 1.5 liter anhydrous ethyl ether. The reaction was stirred for an additional 3 hours and quenched by the dropwise addition of a solution of 400 g potassium carbonate in 1.5 liters water. The layers were separated and the ether layer concentrated in vacuo to provide 2-(trichloroacetyl)pyrrole (1.2 kg, 5.1 mol) as a yellow crystalline solid sufficiently pure to be used without further purification. To a cooled (-40° C.) solution of 2-(trichloroacetyl) pyrrole (1.2 kg, 5.1 mol) in acetic anhydride (6 L) in a 12 L flask equipped with a mechanical stirrer was added 440 mL fuming nitric acid over a period of 1 hour while maintaining a temperature of (-40° C.). The reaction was carefully allowed to warm to room temperature and stir an additional 4 h. The mixture was cooled to -30° C., and isopropyl alcohol (6 L) added. The solution was stirred at -20° C. for 30 min during which time a white precipitate forms. The solution was allowed to stand for 15 min and the resulting precipitate collected by vacuum filtration.

Source