4-Fluorophenol → HCID 58442477, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=2)=[CH:24][CH:23]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 1-(4-chloro-2,6-dimethylphenyl)ethanone (4.50 g, 24.6 mmol), K3PO4 (10.5 g, 49.3 mmol), 4-fluorophenol (3.31 g, 29.5 mmol) in toluene (49.3 mL), was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (314 mg, 0.74 mmol), Pd(OAc)2 (233 mg, 1.04 mmol). The reaction was heated at 100° C. overnight under N2. The solution was cooled to room temperature and filtered through a small pad of diatomaceous earth. The cake was washed with ethyl acetate (100 mL), and combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(4-(4-Fluorophenoxy)-2,6-dimethylphenyl)ethanone (4.40 g) as yellow oil in 68% yield: 1H NMR (500 MHz, CDCl3) δ 7.03 (m, 2 H), 6.98 (m, 2 H), 6.60 (s, 2 H), 2.47 (s, 3 H), 2.22 (s, 6 H).
Workup
- temperatureThe solution was cooled to room temperature
- filtrationfiltered through a small pad of diatomaceous earth
- washThe cake was washed with ethyl acetate (100 mL)
- concentrationwas concentrated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-1ec858a10157489a992b5611d562742a
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999983B2
Reaction notes
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