Reacción #1863

Ecuación de reacción

N-methyl-m-anisidine

triethylamine

toluene

2-bromopropionyl bromide

→

2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otrothe aqueous layer was collected
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   Lavadowashed with 2N HCl
5. 5
   Secadodried (Na2SO4)
6. 6
   OtroThe solvent was evaporated
7. 7
   Otroto yield an oil which
8. 8
   Otrowas purified
9. 9
   workup.DISTILLATIONKugelrohr distillation
10. 10
    workup.DISSOLUTIONThe distillate was dissolved in isopropyl ether
11. 11
    OtroThe solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution

Procedimiento

A solution of N-methyl-m-anisidine (265 g), triethylamine (269 ml) and toluene (550 ml) was stirred at 0° C. as 2-bromopropionyl bromide (202.6 ml) was added dropwise. The mixture was mechanically stirred overnight at room temperature. Water was added to the reaction and the aqueous layer was collected and extracted with ethyl acetate. All organic phases were combined, washed with 2N HCl, and dried (Na2SO4). The solvent was evaporated to yield an oil which was purified using Kugelrohr distillation. The distillate was dissolved in isopropyl ether. The solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution.

Fuente