반응 #90996

반응 방정식

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

수율 91.0%

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

수율 91.0%

용매

DCM

반응 조건

후처리

1. 1
   기타then partitioned between EtOAc and aqueous 1M HCl
2. 2
   세척The organic layer was washed successively with saturated aqueous NaHCO3, water and brine
3. 3
   건조The organic layer was then dried over MgSO4
4. 4
   여과filtered
5. 5
   기타the solvent evaporated in vacuo
6. 6
   기타The residue was triturated from Et2O
7. 7
   여과filtered
8. 8
   세척The filtered solid was washed with methanol
9. 9
   농축the washings were concentrated in vacuo

실험 절차

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−).

출처