Réaction #1135829

Équation de réaction

methyl 8-chloro-8-oxooctanoate

4-bromo-2-nitroaniline

triethylamine

→

methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate

Rendement 81.2%

Solvants

DMF

DMF

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 1 N HCl, saturated sodium bicarbonate solution and brine
2. 2
   ConcentrationThe separated organic layer was concentrated
3. 3
   Autrepurified by biotage column chromatography

Mode opératoire

To a solution of methyl 8-chloro-8-oxooctanoate (229 mg, 1.11 mmol) in DMF at 0° C. was added a solution of 4-bromo-2-nitroaniline (200 mg, 0.922 mmol) and triethylamine (0.37 mL, 2.77 mmol) in DMF drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated and purified by biotage column chromatography to give methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate (290 mg)

Source