N,N-Dimethylaniline → 2-Methylpropyl 2-bromoacetate

Over a period of 6-8 hours there was added dropwise 1 M of bromoacetyl bromide to a stirred solution of 1 M of isobutyl alcohol, 1 M of dimethylaniline and 200 ml of anhydrous ether. The solution was kept just below boiling by adjusting the rate of addition and by occasional cooling in an ice bath. After complete addition, the mixture was stirred overnight at room temperature. Water (100 ml) was added and the mixture stirred until all of the precipitate had dissolved. The layers were separated and the ether layer was washed with 100 ml portions of 10% sulfuric acid until neutralization of the washings resulted in a clear solution. The washed ether solution was dried over anhydrous sodium sulfate and after removal of the drying agent and solvent the residue was distilled in vacuo. The recovered product had a bp / 14 mm = 72° - 76° C, n25 = 1.4468.

1. additionthe rate of addition
2. temperatureby occasional cooling in an ice bath
3. additionAfter complete addition
4. stirringthe mixture stirred until all of the precipitate
5. dissolutionhad dissolved
6. customThe layers were separated
7. washthe ether layer was washed with 100 ml portions of 10% sulfuric acid until neutralization of the washings
8. customresulted in a clear solution
9. dry with materialThe washed ether solution was dried over anhydrous sodium sulfate
10. customafter removal of the drying agent and solvent the residue
11. distillationwas distilled in vacuo
12. custom14 mm = 72° - 76° C, n25 = 1.4468

ORD record

ord-92927251d03047f380878ccb462655d0

Source dataset

uspto-grants-1976_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03995641