1-Chloro-4-(trifluoromethyl)benzene → HCID 67387269, compound
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28](=[O:30])[CH3:29])=[C:23]([CH3:31])[CH:22]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:31][C:23]1[CH:22]=[C:21]([O:20][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH:26]=[C:25]([CH3:27])[C:24]=1[C:28](=[O:30])[CH3:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 1-chloro-4-(trifluoromethyl)benzene (6.60 g, 36.6 mmol), K3PO4 (12.9 g, 60.9 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (5.00 g, 30.5 mmol) in toluene (60.9 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (388 mg, 0.91 mmol) and Pd(OAc)2 (288 mg, 1.28 mmol). The reaction was heated at 100° C. for 120 min under N2. The solution was cooled to room temperature and filtered through a small pad of Celite. The cake was washed with ethyl acetate (50 mL) and combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(2,6-dimethyl-4-(4-(trifluoromethyl)phenoxy)phenyl)ethanone (1.8 g) as yellow oil in 19% yield: 1H NMR (500 MHz, CDCl3) δ 7.58 (d, J=8.5 Hz, 2H), 7.04 (d, J=8.5 Hz, 2H), 6.70 (s, 2H), 2.50 (s, 3H), 2.25 (s, 6H).
Workup
- temperatureThe solution was cooled to room temperature
- filtrationfiltered through a small pad of Celite
- washThe cake was washed with ethyl acetate (50 mL)
- concentrationwas concentrated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-0d7da1db57554fce9ff658a3fd672c81
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409902B2
Reaction notes
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