Potassium Carbonate → 1,3-Dibromo-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Br:8])[CH:7]=1.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>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[CH:5]=[C:6]([Br:8])[CH:7]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3,5-dibromophenylboronic acid (2.58 g, 9.2 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (2.42 g, 13.8 mmol), K2CO3 (2.54 g, 18.4 mmol) and Pd(PPh3)2Cl2 (129 mg, 0.18 mmol) in THF (12 mL) and H2O (6 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 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 to give the crude desired product (2.3 g; 76% yield) as colorless oil.
Workup
- temperatureThe mixture was cooled to rt
- custompartitioned between EA (50 mL) and H2O (50 mL)
- extractionThe aqueous layer was extracted with EA (50 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
Sources & evidence
- ORD record
- ord-20337acf8fc7483b93369406c53a669f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156860B2
Reaction notes
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