1-Chloro-4-(chloromethyl)benzene → 4-(2-Fluoroethoxy)benzyl 4-chlorobenzyl ether
Reaktionsgleichung
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][F:1])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A mixture consisting of 5.3 g of 4-(2-fluoroethoxy)benzyl alcohol, 5.0 g of 4-chlorobenzyl chloride, 0.5 g of triethylbenzylammonium bromide and 20 g of a 50% aqueous solution of sodium hydroxide was stirred at 50° C. for 4 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (200 g) column chromatography (developing solvent: benzene) to give 8.2 g of the desired 4-(2-fluoroethoxy)benzyl 4-chlorobenzyl ether as pale yellow crystals.
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with toluene
- washThe toluene layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customToluene was evaporated under reduced pressure
- customThe resulting crude ether was purified by silica gel (200 g) column chromatography (developing solvent: benzene)
Quellen und Nachweise
- ORD-Eintrag
- ord-ebbb4618413245ad80423353649d1525
- Quelldatensatz
- uspto-grants-1985_11
- Patentnummer
- US04552894
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