Reaction #1863

Reaction equation

N-methyl-m-anisidine

triethylamine

toluene

2-bromopropionyl bromide

→

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

Solvents

Water

Conditions

Workup

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

Procedure

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.

Source