Reaction #6649

Reaction equation

hexane

3,3-dimethylacryloyl chloride

4-bromoaniline

→

title compound

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

Solvents

THF

THF

Conditions

Workup

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

Procedure

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).

Source