Reacción #47533

Ecuación de reacción

3-chloro-but-2-enoic acid ethyl ester

Potassium t-butoxide

3-bromo-phenol

→

(E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester

Rendimiento 39.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturato reflux for 0.75 h
3. 3
   TemperaturaThe reaction mixture was refluxed for an additional 3 h
4. 4
   ConcentraciónAfter this time, the mixture was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with water
6. 6
   Extracciónextracted with diethyl ether
7. 7
   LavadoThe organic layer was then washed with 5% aqueous sodium hydroxide solution
8. 8
   Secadodried over sodium sulfate
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

Potassium t-butoxide (10.5 g, 0.094 mol) was added to a stirred solution of 3-bromo-phenol (8.18 g, 0.047 mol) in tetrahydrofuran (30 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 7.00 g, 0.047 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester (5.20 g, 39%) as a yellow oil.

Fuente