반응 #90999

반응 방정식

4-Ethoxy-3,5-bis(trifluoromethyl)aniline

EDC

4-(Methoxycarbonyl)benzoic acid

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

→

methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate

수율 28.0%

Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate

수율 28.0%

용매

EtOAc

DCM

반응 조건

후처리

1. 1
   세척washed three times with 1 M HCl
2. 2
   세척The organic phase was washed with brine
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   기타the solvent removed in vacuo
6. 6
   기타The residue was purified by silica gel chromatography (10% EtAOc in isohexane)

실험 절차

4-(Methoxycarbonyl)benzoic acid (4) (246 mg, 1.37 mmol) was dissolved in DCM (15 mL) and treated with EDC (654 mg, 3.41 mmol) and DMAP (33 mg, 273 μmol). The resultant mixture was stirred at RT for 15 min. 4-Ethoxy-3,5-bis(trifluoromethyl)aniline (3) (360 mg, 1.32 mmol) was added and the resultant mixture was stirred at RT for 20 h. The mixture was diluted with EtOAc and washed three times with 1 M HCl and then three times with NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (10% EtAOc in isohexane) to afford methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate (5) (150 mg, 28%): m/z 436 [M+H]+ (ES+).

출처