Réaction #4557

Équation de réaction

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

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

potassium carbonate

acetonitrile

→

product

Rendement 58.2%

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

Rendement 58.2%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 16 hours
3. 3
   Extractionextracted with ether
4. 4
   LavageThe combined ether extracts were washed with dilute aqueous NaOH
5. 5
   Lavagewashed with water
6. 6
   Séchagedried over MgSO4
7. 7
   Autrethe solvent was removed by rotary evaporation
8. 8
   AutreThe residue was purified by HPLC
9. 9
   Lavageeluting with 95:5 hexane

Mode opératoire

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.

Source