Реакция #1121787

Уравнение реакции

4-fluorobenzoic acid

diisopropylethylamine

HOBT

HBTU

N,O-dimethyl hydroxylamine hydrochloride

→

4-fluoro-N-methoxy-N-methyl-benzamide

Выход 79.0%

4-Fluoro-N-methoxy-N-methyl-benzamide

Выход 79.0%

Растворители

DMF

EtOAc

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter stirring at room temperature for 2 hours
2. 2
   Промывкаwashed with 4×50 mL of water
3. 3
   КонцентрированиеThe combined organic layers is concentrated
4. 4
   Другоеpurified by flash column chromatography (hexane 70%, EtOAc 30%)

Методика

To a solution of 4-fluorobenzoic acid (6.8 g, 48.57 mmole) in 100 mL of DMF at room temperature, is added diisopropylethylamine (25.3 mL, 145.7 mmole). After stirring at room temperature for 20 minutes, HOBT (7.22 g, 53.43 mmole), HBTU (20.26 g, 53.43 mmole) and N,O-dimethyl hydroxylamine hydrochloride (5.69 g, 58.29 mmole) are added to the reaction solution. After stirring at room temperature for 2 hours, the reaction solution is diluted with 200 mL of EtOAc and washed with 4×50 mL of water. The combined organic layers is concentrated and purified by flash column chromatography (hexane 70%, EtOAc 30%) to yield 4-fluoro-N-methoxy-N-methyl-benzamide (4a) (7.0 g, yield 79%).

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