4-Iodophenol → 4-(3-Trifluoromethylphenyl)phenol
Reaction equation
C(=O)([O-])O.[Na+].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][CH:13]=1.I[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>O1CCOCC1.Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:6][C:7]([F:18])([F:17])[C:8]1[CH:9]=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:11]=[CH:12][CH:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
An aqueous solution of sodium hydrogen carbonate (6.9 g in 18 mL water, 82 mmol) was added to a stirred solution of 3-trifluoromethylbenzeneboronic acid (7.77 g, 41 mmol) and 4-iodophenol (6.0 g, 30 mmol) in 1,4-dioxane (90 mL). The reaction mixture was degassed, then tetrakis(triphenylphosphine) palladium (0) (1.58 g, 1.36 mmol) was added and the reaction mixture heated at 100° C. for 18 hours. The mixture was diluted with a 2M aqueous solution of HCl and extracted with ethyl acetate (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane gradient elution) to afford the title compound (2.17 g, 30%) as an oil.
Workup
- customThe reaction mixture was degassed
- extractionextracted with ethyl acetate (50 mL)
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane gradient elution)
Sources & evidence
- ORD record
- ord-0f79d83225b7446186e4194d4f1a7b87
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772293B2
Reaction notes
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