Réaction #47357

Équation de réaction

3-(2,5-difluoro-phenoxy)-but-2-enoic acid ethyl ester

N-bromosuccinimide

→

4-bromo-3-(2,5-difluoro-phenoxy)-but-2-enoic acid ethyl ester

Rendement 87.2%

Solvants

carbon tetrachloride

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was then heated
2. 2
   TempératureAt this time, the reaction was cooled to 25° C.
3. 3
   Autrewas placed in the refrigerator overnight
4. 4
   AutreAt this time, the reaction was removed from the refrigerator
5. 5
   AutreThe resulting precipitate was removed by filtration
6. 6
   Lavagewas rinsed with carbon tetrachloride (25 mL)
7. 7
   ConcentrationThe filtrate was concentrated in vacuo
8. 8
   AutrePurification by Analogix flash chromatography (40 g, 2% ethyl acetate/hexanes)

Mode opératoire

A solution of 3-(2,5-difluoro-phenoxy)-but-2-enoic acid ethyl ester (1.35 g, 5.57 mmol) in carbon tetrachloride (30.9 mL) was treated with N-bromosuccinimide (1.09 g, 6.13 mmol) and benzoyl peroxide (108 mg, 0.44 mmol). The reaction was then heated to reflux (105° C.) for 5 h. At this time, the reaction was cooled to 25° C. and then was placed in the refrigerator overnight. At this time, the reaction was removed from the refrigerator. The resulting precipitate was removed by filtration and was rinsed with carbon tetrachloride (25 mL). The filtrate was concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 2% ethyl acetate/hexanes) afforded impure 4-bromo-3-(2,5-difluoro-phenoxy)-but-2-enoic acid ethyl ester (1.56 g, 87%) as a clear oil. The material was used without further purification.

Source