반응 #159772

반응 방정식

1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

→

6-bromospiro[4H-1,4-benzoxazine-2,1′-cyclopropane]-3-one

수율 93.2%

용매

acetic acid

ethyl acetate

반응 조건

후처리

1. 1
   온도The mixture was cooled to room temperature
2. 2
   여과filtered through celite bed
3. 3
   농축The filtrate was concentrated
4. 4
   세척washed with water and saturated sodium bicarbonate solution
5. 5
   건조the organic layer was dried over sodium sulfate
6. 6
   농축concentrated
7. 7
   기타the resulting residue was purified by silica gel column chromatography

실험 절차

To a stirred solution of 1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester (3.5 g, 10.6 mmol) in glacial acetic acid (40 mL) was added iron powder (5.9 g, 106.1 mmol) at room temperature and the reaction mixture was heated at 60° C. for 3 h. The mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through celite bed. The filtrate was concentrated, and the resulting residue was taken in ethyl acetate and washed with water and saturated sodium bicarbonate solution, then the organic layer was dried over sodium sulfate, concentrated and the resulting residue was purified by silica gel column chromatography to furnish 6-bromospiro[4H-1,4-benzoxazine-2,1′-cyclopropane]-3-one (2.51 g).

출처