Cesium carbonate → 6-Chloro-4'-fluorobiphenyl-3-ol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1I.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:11][C:12]1[C:17]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 75 °C
Procedure
A solution of 4-fluorophenylboronic acid (500 mg, 3.57 mmol), 4-chloro-3-iodophenol (455 mg, 1.79 mmol) and caesium carbonate (1.75 g) in dioxane (10 mL) and water (5 mL) was degassed 1 hour with nitrogen. Tetrakis(triphenylphosphine)palladium (0) (104 mg, 0.09 mmol) was added and the reaction mixture was heated for 18 hours at 75° C. The cooled reaction mixture was concentrated in vacuo and the residual aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layer were dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20% ethyl acetate in heptane to afford the title compound (280 mg, 70%) as a yellow oil.
Workup
- customThe cooled reaction mixture
- concentrationwas concentrated in vacuo
- extractionthe residual aqueous layer was extracted with ethyl acetate (3×50 mL)
- dry with materialThe combined organic layer were dried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was purified by silica gel chromatography
- washeluting with 20% ethyl acetate in heptane
Sources & evidence
- ORD record
- ord-d8fa635e944240298921f269f1f5ebe6
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772293B2
Reaction notes
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