Potassium Carbonate → 2-Chloro-1-fluoro-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[F:8].Br[C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[CH:5]=[CH:6][C:7]=1[F:8]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of (3-chloro-4-fluorophenyl) boronic acid (300 mg, 1.72 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (331 mg, 1.89 mmol), K2CO3 (474 mg, 3.44 mmol) and Pd(PPh3)2Cl2 (25 mg, 0.035 mmol) in THF (2 mL) and H2O (1 mL) was heated at 80° C. in a sealed tube for 3 h. The mixture was cooled to rt and partitioned between EA (20 mL) and H2O (20 mL). The aqueous layer was extracted with EA (20 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel elute with PE to give 2-chloro-1-fluoro-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (240 mg, 62.3% yield) as colorless oil.
Workup
- temperatureThe mixture was cooled to rt
- custompartitioned between EA (20 mL) and H2O (20 mL)
- extractionThe aqueous layer was extracted with EA (20 mL)
- dry with materialthe combined organic layers were dried over Na2SO4
- customThe solvent was removed under reduced pressure
- customthe crude product was purified by column chromatography on silica gel
- washelute with PE
Sources & evidence
- ORD record
- ord-7d3e6935eb2743069cee5c9eceecf552
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853186B2
Reaction notes
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