Ethyl Acetate → 2-Chloro-1-(4-iodophenoxy)-4-(trifluoromethyl)benzene

HRID 384148

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1F.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:11]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-iodophenol (200 mg) in dimethylsulfoxide (1 ml), 218 mg of 2-chloro-1-fluoro-4-(trifluoromethyl)benzene and 251 mg of potassium carbonate were added, and the reaction solution was stirred at 120° C. for 3 hours. The reaction solution was cooled, ethyl acetate was added, the insoluble matter was filtered off, and the filtrate was washed with water and a saturated saline solution and dried over an anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-80/20)) to afford the title compound as a colorless oil.

Workup

temperatureThe reaction solution was cooled
filtrationthe insoluble matter was filtered off
washthe filtrate was washed with water
dry with materiala saturated saline solution and dried over an anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue obtained
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-80/20))

Sources & evidence

ORD record: ord-236a00b7ed9d4ccda644ca54e62e3c55
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367708B2

Linked notes

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