Reaktion #4557

Reaktionsgleichung

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

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

potassium carbonate

acetonitrile

→

product

Ausbeute 58.2%

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

Ausbeute 58.2%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 16 hours
3. 3
   Extraktionextracted with ether
4. 4
   WaschenThe combined ether extracts were washed with dilute aqueous NaOH
5. 5
   Waschenwashed with water
6. 6
   Trocknendried over MgSO4
7. 7
   Sonstigethe solvent was removed by rotary evaporation
8. 8
   SonstigeThe residue was purified by HPLC
9. 9
   Wascheneluting with 95:5 hexane

Vorschrift

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.

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