Cesium carbonate → 3-(2-Chloro-4-phenoxyphenoxy)-propanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:15].Br[CH2:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:15][CH2:17][CH2:18][CH2:19][OH:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a 100 ml DMF solution of 2-chloro-4-phenoxyphenol (10 g, 45 mmol) were added 3-bromopropanol (8.2 ml, 91 mmol) and cesium carbonate (6.2 g, 50 mmol). The resulting suspension was heated to 70° C. for 7 hr. Solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 30% AcOEt/hexanes gave 3-(2-chloro-4-phenoxyphenoxy)-propanol 11.96 g (95%). This material was dissolved in acetonitrile 200 ml. To it was added triphenylphosphine (18.5 g, 55.8 mmol) and carbon tetrabromide (16.9 g, 64.4 mmol). After stirring at rt for 1 hr, the solvent was removed, and the residue was chromatographed on silica gel. Elution with 5% THF/hexanes gave the title compound as colorless oil 10.9 g (74%).
Workup
- customSolvent was removed under reduced pressure
- additionThe residue was diluted with AcOEt and water
- customThe organic layer was separated
- extractionThe aqueous layer was extracted twice with AcOEt
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel
- washElution with 30% AcOEt/hexanes
Sources & evidence
- ORD record
- ord-c3069c81e74b489382b904c9e630e86c
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06645997B2
Reaction notes
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