반응 #470432

반응 방정식

CaCO3

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

iodine monochloride

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

용매

MeOH

CH2Cl2

반응 조건

후처리

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

실험 절차

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 monochloride (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.

출처