Reacción #58832

Ecuación de reacción

N-methoxymethanamine hydrochloride

diisopropyl ethyl amine

3-bromobenzoyl chloride

→

3-bromo-N-methoxy-N-methylbenzamide

Rendimiento 90.3%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated under vacuum
2. 2
   workup.ADDITIONThe resultant residue was dispersed in water
3. 3
   Extracciónextracted with ethyl ether
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe resultant residue was purified on silica gel (Biotage)

Procedimiento

A mixture of N-methoxymethanamine hydrochloride (22.1 g, 228.5 mmol), diisopropyl ethyl amine (63.5 mL, 365.6 mmol) and CH2Cl2 was treated dropwise with 3-bromobenzoyl chloride (15 g, 68.5 mmol) in CH2Cl2, stirred at room temperature for 30 minutes, and concentrated under vacuum. The resultant residue was dispersed in water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (Biotage) using hexanes/EtOAc (2/1) as the eluting solvents to give 3-bromo-N-methoxy-N-methylbenzamide as a tan solid (15.1 g, 90% yield).

Fuente