反应详情

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−).

1. customthen partitioned between EtOAc and aqueous 1M HCl
2. washThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
3. dry with materialThe organic layer was then dried over MgSO4
4. filtrationfiltered
5. customthe solvent evaporated in vacuo
6. customThe residue was triturated from Et2O
7. filtrationfiltered
8. washThe filtered solid was washed with methanol
9. concentrationthe washings were concentrated in vacuo