Reaktion #6649

Reaktionsgleichung

hexane

3,3-dimethylacryloyl chloride

4-bromoaniline

→

title compound

N-(4-Bromophenyl)3,3-dimethylacrylamide

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Extraktionthe aqueous layer was extracted with 2×50 ml of hexanes
3. 3
   Waschenwashed successively with 30 ml of water and 2×30 ml of saturated NaCl solution
4. 4
   Trocknendried (MgSO4)
5. 5
   SonstigeThe solvent was removed in vacuo
6. 6
   Sonstigethe residue purified by recrystallization from an ethyl acetate and hexanes mixture

Vorschrift

To a solution of 9.48 g (80 mmol) of 3,3-dimethylacryloyl chloride in 200 ml of dry THF was added with vigorous shaking a solution of 13.76 g (80 mmol) of 4-bromoaniline in 300 ml of dry THF. The mixture was stood at room temperature for 2 h and then treated with 80 g of ice followed by 200 ml of hexane. The organic layer was separated and the aqueous layer was extracted with 2×50 ml of hexanes. The organic layers were combined and washed successively with 30 ml of water and 2×30 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by recrystallization from an ethyl acetate and hexanes mixture to give the title compound as colorless crystals. PMR (CDCl3): δ 1.91 (3H, s), 2.23 (3H, s), 5.73 (1H, broad s), 7.38-7.55 (5H, m).

Quelle