تفاعل #6649

معادلة التفاعل

hexane

3,3-dimethylacryloyl chloride

4-bromoaniline

→

title compound

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر