Reaktion #90996

Reaktionsgleichung

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

Ausbeute 91.0%

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

Ausbeute 91.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen partitioned between EtOAc and aqueous 1M HCl
2. 2
   WaschenThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
3. 3
   TrocknenThe organic layer was then dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent evaporated in vacuo
6. 6
   SonstigeThe residue was triturated from Et2O
7. 7
   Filtrationfiltered
8. 8
   WaschenThe filtered solid was washed with methanol
9. 9
   Einengenthe washings were concentrated in vacuo

Vorschrift

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−).

Quelle