4-Bromoaniline → 2-Butenamide, N-(4-bromophenyl)-3-methyl-

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).

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted with 2×50 ml of hexanes
3. washwashed successively with 30 ml of water and 2×30 ml of saturated NaCl solution
4. dry with materialdried (MgSO4)
5. customThe solvent was removed in vacuo
6. customthe residue purified by recrystallization from an ethyl acetate and hexanes mixture

ORDレコード

ord-6b77fd970be54f8dbe3fb67395b6565b

出典データセット

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05248777