تفاعل #90996

معادلة التفاعل

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

المردود 91.0%

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

المردود 91.0%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىthen partitioned between EtOAc and aqueous 1M HCl
2. 2
   غسيلThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
3. 3
   تجفيفThe organic layer was then dried over MgSO4
4. 4
   ترشيحfiltered
5. 5
   أخرىthe solvent evaporated in vacuo
6. 6
   أخرىThe residue was triturated from Et2O
7. 7
   ترشيحfiltered
8. 8
   غسيلThe filtered solid was washed with methanol
9. 9
   تركيزthe washings were concentrated in vacuo

الإجراء التجريبي

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−).

المصدر