Реакция #587742

Уравнение реакции

4-azido-5-bromo-2-(2,4-dichlorophenylamino)-3-fluorobenzoic acid methyl ester

→

desired product

Выход 64.4%

4-amino-5-bromo-2-(2,4-dichlorophenylamino)-3-flourobenzoic acid methyl ester

Выход 64.4%

Растворители

AcOH CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   Промывкаwashed with water, saturated aqueous NaHCO3 (2×), water, and brine
2. 2
   СушкаThe organic layer was dried over MgSO4
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   Другоеto give the crude material which
6. 6
   Другоеwas purified by silica gel flash column chromatography(3 to 5% EtOAc in hexanes)

Методика

To a mixture of 4-azido-5-bromo-2-(2,4-dichlorophenylamino)-3-fluorobenzoic acid methyl ester (2.05 g, 4.72 mmol) in AcOH-CH2Cl2 (10-30 mL) was added Zn dust (1.59 g, 24.3 mmol) at 0° C. The reaction mixture was warmed to room temperature. The resulting mixture was stirred for 1 hour. The reaction mixture was diluted with CH2Cl2, and washed with water, saturated aqueous NaHCO3 (2×), water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the crude material which was purified by silica gel flash column chromatography(3 to 5% EtOAc in hexanes) to afford the desired product (1.24 g, 64%).

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