Reaction equation
CC1C=CC(C)=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([F:19])[CH:18]=1)[C:13](Cl)=O.[C:20]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=C)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].CN1CCOCC1>CC([O-])=O.CC([O-])=O.[Pd+2].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.CCOC(C)=O>[C:20]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[CH:13][C:12]2[CH:11]=[C:10]([F:9])[CH:18]=[C:17]([F:19])[CH:16]=2)=[CH:26][CH:25]=1)(=[O:22])[CH3:21]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
A 25 mL round bottom flask was charged with p-xylene (10 mL), Pd(OAc)2 (11.3 mg, 0.05 mmol), 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (21.4 mg, 0.05 mmol), 3,5-difluorobenzoyl chloride (0.89 g, 5 mmol), 4-acetoxystyrene (0.97 g, 6 mmol), and N-methyl morpholine (0.69 g, 6 mmol). The mixture was stirred at 120° C. for 3.5 h under nitrogen atmosphere. Then it was cooled to room temperature and EtOAc was added and filtered. The filtrate was washed with brine and dried over Na2SO4. Then it was filtered and purified via flash chromatography and gave the product (1.02 g, 74%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.51 (d, J=8.4 Hz, 2H), 7.12-6.97 (m, 6H), 6.70 (t, 1H), 2.31 (s, 3H).
Workup
- temperatureThen it was cooled to room temperature
- filtrationfiltered
- washThe filtrate was washed with brine
- dry with materialdried over Na2SO4
- filtrationThen it was filtered
- custompurified via flash chromatography
Sources & evidence
- ORD record
- ord-999fdb07a7264857b0b22f06af7d7172
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841477B2
Linked notes
Loading…