Reaktion #323163

Reaktionsgleichung

methanesulfonate

methyl lactate

potassium carbonate

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

→

oil

Ausbeute 189.6%

2-[4-(4-bromo-2-fluorophenoxy)phenoxy]-propionic acid methyl ester

Ausbeute 189.6%

Lösungsmittel

water

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ether (2×200 ml)
2. 2
   workup.ADDITIONPentane (100 ml) was added to the combined ether extracts
3. 3
   Waschenthe resulting solution washed with water (300 ml)
4. 4
   TrocknenThe organic phase was dried (MgSO4)
5. 5
   Sonstigethe solvent evaporated

Vorschrift

A mixture of the 4-(4-bromo-2-fluorophenoxy)-phenol (2.83 g, 0.01 mol), the methanesulfonate of S methyl lactate (18.2 g, 0.01 mol), and potassium carbonate (1.67 g, 0.012 mol) in DMSO (70 ml) was stirred at room temperature for 40 hours, then poured into water (700 ml). The mixture was extracted with ether (2×200 ml). Pentane (100 ml) was added to the combined ether extracts and the resulting solution washed with water (300 ml). The organic phase was dried (MgSO4) and the solvent evaporated to give a light yellow oil (~7 g). This oil was purified via prep HPLC (8:2 hexane-acetone) with the first peak being collected. Removal of the solvent gave the desired product enriched in the "R" enantiomer; Optical rotation=+20.34° @ 25° C. RI=1.5614 @ 25° C.; NMR (CDCl3) was identical with that obtained in Example 4. No attempt was made to determine the optical purity of this material.

Quelle