Water → 2-Chloro-2'-fluoro-5-methoxybiphenyl
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[Cl:20].C(=O)([O-])[O-].[Cs+].[Cs+].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].O1CCOCC1>[Cl:20][C:13]1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Tetrakistriphenylphosphinepalladium (0) (229 mg, 0.20 mmol) was added to a degassed mixture of 2-fluorophenylboronic acid (556 mg, 3.97 mmol), 2-bromo-1-chloro-4-methoxybenzene (0.49 mL, 3.57 mmol), caesium carbonate (3.87 g, 11.9 mmol), water (5.0 mL) and dioxane (26.0 mL). The reaction was heated at 80° C. for 18 hours, cooled to room temperature and then partitioned between ethyl acetate (30.0 mL) and sat. aq. ammonium chloride (10.0 mL). The aqueous phase was separated and extracted with ethyl acetate (2×10 mL). The combined organic phases were washed with brine (5.0 mL), dried over MgSO4, filtered and evaporated to give a pale yellow oil. Column chromatography purification on silica, eluting with heptanes gave the title compound (749 mg, 88%) as a colourless oil.
Workup
- temperaturecooled to room temperature
- custompartitioned between ethyl acetate (30.0 mL) and sat. aq. ammonium chloride (10.0 mL)
- customThe aqueous phase was separated
- extractionextracted with ethyl acetate (2×10 mL)
- washThe combined organic phases were washed with brine (5.0 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customto give a pale yellow oil
- customColumn chromatography purification on silica
- washeluting with heptanes
Sources & evidence
- ORD record
- ord-d8d4b2361e5147d793efdc9c007bc1eb
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772293B2
Reaction notes
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