Reaktion #1863

Reaktionsgleichung

N-methyl-m-anisidine

triethylamine

toluene

2-bromopropionyl bromide

→

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

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle