Reacción #1121787

Ecuación de reacción

4-fluorobenzoic acid

diisopropylethylamine

HOBT

HBTU

N,O-dimethyl hydroxylamine hydrochloride

→

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

Rendimiento 79.0%

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

Rendimiento 79.0%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente