Reaktion #90999

Reaktionsgleichung

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

Ausbeute 28.0%

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

Ausbeute 28.0%

Lösungsmittel

EtOAc

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed three times with 1 M HCl
2. 2
   WaschenThe organic phase was washed with brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent removed in vacuo
6. 6
   SonstigeThe residue was purified by silica gel chromatography (10% EtAOc in isohexane)

Vorschrift

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+).

Quelle