反応 #6649

反応方程式

hexane

3,3-dimethylacryloyl chloride

4-bromoaniline

→

title compound

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

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The organic layer was separated
2. 2
   抽出the aqueous layer was extracted with 2×50 ml of hexanes
3. 3
   洗浄washed successively with 30 ml of water and 2×30 ml of saturated NaCl solution
4. 4
   乾燥dried (MgSO4)
5. 5
   その他The solvent was removed in vacuo
6. 6
   その他the residue purified by recrystallization from an ethyl acetate and hexanes mixture

実験手順

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).

出典