Reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].F[C:14](OB([O-])[O-])=[C:15](F)F.[K+].[K+]>C(O)(C)C.O.C(N)(C)(C)C>[F:10][C:9]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:2]=1[CH:14]=[CH2:15])[NH2:6]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
In 20 mL of isopropanol, 10 mL of water and 5 mL of t-butylamine, 4.0 g (16.7 mmol) of 4-bromo-3-(trifluoromethyl)aniline was dissolved, and 4.0 g (29.9 mmol) of potassium (trifluoro)vinylborate and 300 mg (0.37 mmol) of PdCl2(dppf)2•2(dichloromethane) complex were added thereto, and the mixture solution was stirred in an argon atmosphere at 80° C. for 20 hours. The reaction solution was concentrated and the residue was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was purified by a silica gel column (n-hexane:ethyl acetate=6:1) to obtain 2.475 g (79%) of a target product as a pale yellow oil.
Workup
- concentrationThe reaction solution was concentrated
- customthe residue was partitioned between water and ethyl acetate
- washthe organic layer was washed with a saturated sodium chloride solution
- concentrationconcentrated under reduced pressure
- customThe product was purified by a silica gel column (n-hexane:ethyl acetate=6:1)
Sources & evidence
- ORD record
- ord-744a22c9d51640a2a06e84a07a95c9aa
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609656B2
Linked notes
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