4-(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=O)=[CH:16][CH:15]=2)=[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. After the reaction mixture had turned to clear solution it was stirred for 15 min at 0° C., then a solution of 4-{[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. The mixture was quenched with saturated NH4Cl, and then concentrated. The residue was dissolved in ethyl acetate (100 mL) and washed with water, and brine. The mixture was dried over anhydrous sodium sulfate and concentrated. Purification via ISCO afforded the title compound (3.0 g).
Workup
- temperatureThe reaction mixture was warmed to rt
- stirringstirred for 1 h
- customThe mixture was quenched with saturated NH4Cl
- concentrationconcentrated
- dissolutionThe residue was dissolved in ethyl acetate (100 mL)
- washwashed with water, and brine
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customPurification via ISCO
Sources & evidence
- ORD record
- ord-0defce345ded46ac9f7163e409ed126c
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273054B2
Reaction notes
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