Reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>>[F:14][C:15]([F:24])([F:25])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:12][CH:13]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 3.13 g of 4-(4-hydroxyphenoxy)butan-1-ol, 4.97 g of 4-(trifluoromethoxy)bromobenzene, and 4.75 g of K2CO3 are placed in a flask and flushed with N2 gas. To this are added 17 ml of pyridine and, after heating to 90° C., 3.42 g of CuO. The reaction mixture is heated at reflux for 2 days, and then cooled and poured into an ice/3N HCl mixture. This mixture is extracted twice with ether; and after separating, the combined ether extracts are washed with saturated NaHCO3, followed by brine, and then dried over MgSO4. Filtration and evaporation yields an oily residue which is purified by flash chromatography on silica gel, using 2:1 hexane/EtOAc as eluant. After evaporation, 4-[4-(4-(trifluoromethoxyphenoxy)phenoxy]butan-1-ol is obtained as a white solid.
Workup
- customare placed in a flask
- customflushed with N2 gas
- additionTo this are added 17 ml of pyridine
- temperatureThe reaction mixture is heated
- temperatureat reflux for 2 days
- temperaturecooled
- additionpoured into an ice/3N HCl mixture
- extractionThis mixture is extracted twice with ether
- customand after separating
- washthe combined ether extracts are washed with saturated NaHCO3
- dry with materialdried over MgSO4
- filtrationFiltration and evaporation
- customyields an oily residue which
- customis purified by flash chromatography on silica gel
- customAfter evaporation
Sources & evidence
- ORD record
- ord-4e8cbc51bc67495bb37ccd36a1e86950
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05412137
Linked notes
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