Water → 4′-Chloro-3′-(trifluoromethyl)[1,1′-biphenyl]-4-ol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].I[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.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:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
4-Chloro-3-(trifluoromethyl)phenylboronic acid (448 mg, 2 mmol) and 4-iodophenol (440 mg, 2 mmol) were dissolved in dioxane (10 mL). Caesium carbonate (1.95 g, 6 mmol), water (2 mL) and tetrakis(triphenylphosphine)palladium (0) (231 mg, 0.2 mmol) were added and the reaction stirred at 80° C. for 1 hour. The reaction was quenched with 2M HCl (5 mL) and partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate was separated, dried over MgSO4 and evaporated. The crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 80:20 to give the title compound (150 mg, 0.55 mmol, 27%) as a white solid.
Workup
- customThe reaction was quenched with 2M HCl (5 mL)
- custompartitioned between ethyl acetate (50 mL) and water (50 mL)
- customThe ethyl acetate was separated
- dry with materialdried over MgSO4
- customevaporated
- customThe crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 80:20
Sources & evidence
- ORD record
- ord-3307399c6f5a4f26bf5a0fc075e89d7a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772293B2
Reaction notes
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