Methyl Lactate → 2-[4-(4-Bromo-2-fluorophenoxy)phenoxy]propionic acid methyl ester
Reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([F:16])[CH:3]=1.CS([O-])(=O)=O.[C:22]([O:27][CH3:28])(=[O:26])[CH:23]([CH3:25])O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:23]([CH3:25])[C:22]([O:27][CH3:28])=[O:26])=[CH:11][CH:12]=2)=[C:4]([F:16])[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (2.83 g, 0.01 mole), the methanesulfonate of S methyl lactate (18.2 g, 0.01 mole), and potassium carbonate (1.67 g, 0.012 mole) 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 desired product enriched in the "R" enantiomer; Optical rotation=+20.34°@25° C. R.I.=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.
Workup
- extractionThe mixture was extracted with ether (2×200 ml)
- additionPentane (100 ml) was added to the combined ether extracts
- washthe resulting solution washed with water (300 ml)
- dry with materialThe organic phase was dried (MgSO4)
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-4044ca45936c46d0834c22ea80c8d88d
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808750
Reaction notes
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