methyl 5-chloro-2-[(2-chloroacetyl)amino]benzoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.59 g (11.5 mmol) of potassium carbonate was added to a DMF (20 mL) solution comprising 1.00 g (3.82 mmol) of methyl 5-chloro-2-[(chloroacetyl)amino]benzoate and 574 mg (3.82 mmol) of 3-tert-butylphenol. The mixture was stirred at 80° C. for 7 hours, and then cooled to room temperature. Water and ethyl acetate were added thereto, and extraction was performed. Thereafter, the organic layer was separated, washed with saturated saline, dried over sodium sulfate, and filtered. After the filtrate was condensed, the obtained crude product was separated and purified by silica gel column chromatography, thereby giving 429 mg of methyl 2-{[(3-tert-butylphenoxy)acetyl]amino}-5-chlorobenzoate (yield: 30%). cooled to room temperature extraction Thereafter, the organic layer was separated washed with saturated saline dried over sodium sulfate filtered condensed the obtained crude product was separated purified by silica gel column chromatography

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.59 g (11.5 mmol) of potassium carbonate was added to a DMF (20 mL) solution comprising 1.00 g (3.82 mmol) of methyl 5-chloro-2-[(chloroacetyl)amino]benzoate and 0.66 g (3.82 mmol) of bromophenol, and the mixture was heated while stirring at 80° C. for 2 hours. The mixture was cooled to room temperature, and water and ethyl acetate were added thereto. After the mixture was extracted, the organic layer was separated, washed with saturated saline, dried over sodium sulfate, filtered, condensed, and dried under reduced pressure. IPE was added to the residue, and powders were collected by filtration, washed with IPE, and dried under reduced pressure at 50° C. for 5 hours, thereby giving 1.11 g of methyl 2-{[(3-bromophenoxy)acetyl]amino-}-5-chlorobenzoate (yield: 73%). the mixture was heated The mixture was cooled to room temperature After the mixture was extracted the organic layer was separated washed with saturated saline dried over sodium sulfate filtered condensed dried under reduced pressure IPE was added to the residue, and powders were collected by filtration washed with IPE dried under reduced pressure at 50° C. for 5 hours