Reacción #4557

Ecuación de reacción

4-(4-bromo-2-fluorophenoxy)phenol

methyl 4-bromo-3-methoxy-2-pentenoate

potassium carbonate

acetonitrile

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product

Rendimiento 58.2%

4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester

Rendimiento 58.2%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 16 hours
3. 3
   Extracciónextracted with ether
4. 4
   LavadoThe combined ether extracts were washed with dilute aqueous NaOH
5. 5
   Lavadowashed with water
6. 6
   Secadodried over MgSO4
7. 7
   Otrothe solvent was removed by rotary evaporation
8. 8
   OtroThe residue was purified by HPLC
9. 9
   Lavadoeluting with 95:5 hexane

Procedimiento

A mixture of 12.0 g (42.4 mmol) 4-(4-bromo-2-fluorophenoxy)phenol, 9.5 g (42.4 mmol) methyl 4-bromo-3-methoxy-2-pentenoate, 6.45 g (46.6 mmol) potassium carbonate and 180 ml acetonitrile was heated at reflux for 16 hours. The mixture was poured into water and extracted with ether. The combined ether extracts were washed with dilute aqueous NaOH, washed with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC eluting with 95:5 hexane:acetone, to give 10.5 g (58 percent) of the product as a clear colorless oil. Calc: C, 53.66; H, 4.27. Found: C, 53.28, H, 4.40. Structure was established on the basis of IR and NMR analysis.

Fuente