benzyl 3-chloro-1H-pyrrole-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-chloro-1H-pyrrole-2-carboxylic acid (15 g, 0.1 mol) in N,N-dimethylformamide (300 mL) and triethylamine (72 mL, 0.52 mmol) under argon atmosphere was added benzyl bromide (61 mL, 0.52 mmol) at 0-5° C. and the reaction was stirred mechanically overnight at room temperature. Next day, the reaction mixture was concentrated in vacuum and the residue was suspended in 4% aqueous solution of sodium bicarbonate (300 mL) and extracted with ethyl acetate (2×250 mL). The organic layers were mixed and washed with more 4% aqueous solution of sodium bicarbonate, water and brine, and were dried (magnesium sulphate, MgSO4) and concentrated under reduced pressure to give 21.4 g of a residue corresponding to the title compound (88% yield). Next day, the reaction mixture was concentrated in vacuum extracted with ethyl acetate (2×250 mL) The organic layers were mixed washed with more 4% aqueous solution of sodium bicarbonate, water and brine were dried (magnesium sulphate, MgSO4) concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-chloro-1H-pyrrole-2-carboxylic acid (15 g, 0.1 mol) in N,N-dimethylformamide (300 mL) and triethylamine (72 mL, 0.52 mmol) under argon atmosphere was added benzyl bromide (61 mL, 0.52 mmol) at 0-5° C. and the reaction was stirred mechanically overnight at room temperature. Next day, the reaction mixture was concentrated in vacuum and the residue was suspended in 4% aqueous solution of sodium bicarbonate (300 mL) and extracted with ethyl acetate (2×250 mL). The organic layers were mixed and washed with more 4% aqueous solution of sodium bicarbonate, water and brine, and were dried (magnesium sulphate, MgSO4) and concentrated under reduced pressure to give 21.4 g of a residue corresponding to the title compound (88% yield). Next day, the reaction mixture was concentrated in vacuum extracted with ethyl acetate (2×250 mL) The organic layers were mixed washed with more 4% aqueous solution of sodium bicarbonate, water and brine were dried (magnesium sulphate, MgSO4) concentrated under reduced pressure