(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde → 1-Chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzene
Reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:21]=CC=C[C:15]=2[CH:16]=O)=[CH:9][C:8]=1[C:22]([F:25])([F:24])[F:23]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH:4]([C:3]1[CH:2]=[CH:21][C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[C:8]([C:22]([F:24])([F:23])[F:25])[CH:9]=2)=[CH:15][CH:16]=1)=[CH2:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of methyl(triphenyl)phosphonium bromide (5.56 g, 15.57 mmol) in anhydrous tetrahydrofuran (THF) (50 mL) was added BuLi (9.5 ml, 15.20 mmol) dropwise at 0° C. The reaction mixture was turned to clear and stirred for 15 min at 0° C., then a solution of -{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzaldehyde (4.07 g, 13.54 mmol) in THF (10 mL) was added. The reaction mixture was warmed to rt and stirred for 1 h, quenched by sat. NH4Cl, and then concentrated. The residue was dissolved in ethyl acetate (100 mL), washed with water, and brine, dried over anhydrous sodium sulfate, concentrated. Purification via ISCO afforded the title compound (3.0 g).
Workup
- temperatureThe reaction mixture was warmed to rt
- stirringstirred for 1 h
- customquenched by sat. NH4Cl
- concentrationconcentrated
- dissolutionThe residue was dissolved in ethyl acetate (100 mL)
- washwashed with water, and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customPurification via ISCO
Sources & evidence
- ORD record
- ord-c07d1c13a6c84b7385b89a4e3d4b19a6
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975400B2
Reaction notes
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