Imidazole → 4-Chloro-3-(trifluoromethyl)phenyl 4-(2-iodoethyl)phenyl ether
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I-:46]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][I:46])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To the solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol (80 mg, 0.253 mmol) in DCM (2.5 ml), was added Ph3P (133 mg, 0.505 mmol), imidazole (34.4 mg, 0.505 mmol) and iodide (128 mg, 0.505 mmol) at 0° C., The mixture was stirred at 0° C. for 10 min, then at room temperature for 1 h. The reaction was quenched with sat. Na2SO3 solution. The aqueous phase was extracted with DCM. The combined organic phase was washed with brine, dried over Na2SO4, concentrated and purified via flash chromatography to afford the title compound (50 mg, 46.4% yield) as colorless oil. LCMS: rt=4.47 min
Workup
- waitat room temperature for 1 h
- customThe reaction was quenched with sat. Na2SO3 solution
- extractionThe aqueous phase was extracted with DCM
- washThe combined organic phase was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- custompurified via flash chromatography
Sources & evidence
- ORD record
- ord-4eaf3061f9df4aaf8abff7f5b3751887
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637536B2
Reaction notes
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