Réaction #4554

Équation de réaction

methanesulfonate

methyl lactate

potassium carbonate

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

→

oil

Rendement 189.6%

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

Rendement 189.6%

Solvants

water

DMSO

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source