Reacción #90996

Ecuación de reacción

3,5-Dibromo-4-ethoxyaniline

triethylamine

4-(Chlorocarbonyl)benzoic acid methyl ester

4-(3,5-dichloro-4-hydroxyphenylcarbamoyl)benzoic acid

→

methyl 4-(3,5-dibromo-4-ethoxyphenylcarbamoyl)benzoate

Rendimiento 91.0%

Methyl 4-(3,5-dibromo-4-ethoxyphenylcarbamoyl)benzoate

Rendimiento 91.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothen partitioned between EtOAc and aqueous 1M HCl
2. 2
   LavadoThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
3. 3
   SecadoThe organic layer was then dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvent evaporated in vacuo
6. 6
   OtroThe residue was triturated from Et2O
7. 7
   Filtraciónfiltered
8. 8
   LavadoThe filtered solid was washed with methanol
9. 9
   Concentraciónthe washings were concentrated in vacuo

Procedimiento

3,5-Dibromo-4-ethoxyaniline (2) (100 mg, 339 μmol) was dissolved in DCM (2.5 mL) and treated with triethylamine (143 μL, 1.02 mmol). 4-(Chlorocarbonyl)benzoic acid methyl ester (3) (135 mg, 678 μmol) was added in one portion and the resultant dark orange mixture was stirred at RT for 3 h then partitioned between EtOAc and aqueous 1M HCl. The organic layer was washed successively with saturated aqueous NaHCO3, water and brine. The organic layer was then dried over MgSO4, filtered and the solvent evaporated in vacuo. The residue was triturated from Et2O and filtered. The filtered solid was washed with methanol and the washings were concentrated in vacuo to provide methyl 4-(3,5-dibromo-4-ethoxyphenylcarbamoyl)benzoate (4) (141 mg, 73%) as a pale brown solid: m/z 456 [M−H]− (ES−).

Fuente