1,3-Cyclohexanedione → 3-Oxo-1-cyclohexenyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate

Participants

Reaction Steps

0.400 g (1.10 mmol) of 2,4-dibromo-3-(aminocarbonylmethoxy)benzoic acid, 0.140 g (1.20 mmol) of cyclohexane-1,3-dione, 0.222 g (1.10 mmol) of N′-(3-dimethyl-aminopropyl) -N-ethylcarbodiimide hydrochloride and 0.001 g of DMAP was stirred for 14 hours at RT in 15 ml of CH2Cl2. The mixture was subsequently diluted with CH2Cl2 and with 0.5 N HCl, and washed with water, with saturated NaHCO3 solution and again with water. After the combined organic phases have been dried over Na2SO4 and concentrated completely, 3-oxo-1-cyclohexenyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate was obtained as a yellow resin, which had sufficient purity for the subsequent reaction.

Provenance & Evidence