تفاعل #159772

معادلة التفاعل

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

→

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

المردود 93.2%

المذيبات

acetic acid

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled to room temperature
2. 2
   ترشيحfiltered through celite bed
3. 3
   تركيزThe filtrate was concentrated
4. 4
   غسيلwashed with water and saturated sodium bicarbonate solution
5. 5
   تجفيفthe organic layer was dried over sodium sulfate
6. 6
   تركيزconcentrated
7. 7
   أخرىthe resulting residue was purified by silica gel column chromatography

الإجراء التجريبي

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).

المصدر