反応 #1340621

反応方程式

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

溶媒

MeOH

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   濃縮The reaction mixture was concentrated
3. 3
   その他partitioned between EtOAc and water
4. 4
   濃縮The organic layer was concentrated
5. 5
   その他purified by flash column chromatography (silica gel, 20-25% EtOAc/hexanes)

実験手順

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.

出典