Réaction #1121787

Équation de réaction

4-fluorobenzoic acid

diisopropylethylamine

HOBT

HBTU

N,O-dimethyl hydroxylamine hydrochloride

→

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

Rendement 79.0%

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

Rendement 79.0%

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source