Reacción #1340621

Ecuación de reacción

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

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente