تفاعل #1340621

معادلة التفاعل

iodine

CH2Cl2

CaCO3

Methyl 4-amino-2-chloro-5-iodo-benzoate

70n

methyl 4-amino-2-chloro-5-iodo-benzoate

→

methyl 4-amino-2-chloro-3-iodo-benzoate

methyl 4-amino-2-chloro-5-iodo-benzoate

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   تركيزThe reaction mixture was concentrated
3. 3
   أخرىpartitioned between EtOAc and water
4. 4
   تركيزThe organic layer was concentrated
5. 5
   أخرىpurified by flash column chromatography (silica gel, 20-25% EtOAc/hexanes)

الإجراء التجريبي

Methyl 4-amino-2-chloro-5-iodo-benzoate, 70n. To a suspension of compound 70m (1.18 g, 6.38 mmol) and CaCO3 (12.8 mmol, 1.28 g) in MeOH (13 mL) was added a solution of iodine monchloride (6.70 mmol, 1.09 g) in CH2Cl2 (6 mL) dropwise at room temperature. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated and then partitioned between EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 20-25% EtOAc/hexanes) to provide methyl 4-amino-2-chloro-5-iodo-benzoate 70n as major the product and methyl 4-amino-2-chloro-3-iodo-benzoate 70o as the minor product.

المصدر