Cesium fluoride → HCID 66791039, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C@H:9]([CH3:12])[CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[F:13].[F-].[Cs+].[CH2:16]([Sn](CCCC)(CCCC)C=C)[CH2:17]CC>O1CCOCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[F:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C@H:9]([CH3:12])[CH2:10][CH3:11])=[CH:7][C:2]=1[CH:16]=[CH2:17]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-chloro-1-fluoro-4-{[(1R)-1-methylpropyl]oxy}benzene (1.75 g, 8.64 mmol) in dioxane (28.8 ml) under argon were added bis(tri-t-butylphosphine) palladium(0) (0.221 g, 0.432 mmol) and cesium fluoride (2.89 g, 19.0 mmol). Argon was bubbled through the reaction for 2 min. To the reaction was added tributyl (vinyl) tin (3.03 ml, 10.4 mmol) and the argon bubbled for another 5 min. The reaction was sealed and heated to 100° C. overnight. The reaction was partitioned between H2O and EtOAc. The aqueous phase was extracted with EtOAc (3 times). The combined organics were dried with MgSO4, filtered, and concentrated. The residue was purified by column chromatography on a silica gel cartridge (0% EtOAc/hexanes to 4% EtOAc/hexanes) to give the desired product.
Workup
- customArgon was bubbled through the reaction for 2 min
- customthe argon bubbled for another 5 min
- customThe reaction was sealed
- customThe reaction was partitioned between H2O and EtOAc
- extractionThe aqueous phase was extracted with EtOAc (3 times)
- dry with materialThe combined organics were dried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography on a silica gel cartridge (0% EtOAc/hexanes to 4% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-215244ea22204f169925aac1b1d9c645
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211904B2
Reaction notes
Loading…