2-Chlorobenzonitrile → 2-Cyano-4'-methylbiphenyl
Reaction equation
[F-].[Cs+].Cl[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[C:12]1([CH3:21])[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1>O1CCOCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[C:15]1[CH:16]=[CH:17][C:12]([CH3:21])=[CH:13][CH:14]=1)#[N:7]Participants
Procedure
7.65 mg of Pd2 (dba)3 (8.35 μmol) and 11.60 mg of Ligand 2 (33.33μmol) were combined in 5 ml of solvent (dioxane, toluene, or 2-propanone) and stirred at room temperature for 2 hours to form a catalyst solution that was used in this example and other examples. CsF (2.28 g, 15.0 mmol), 2-chlorobenzonitrile (0.689 g, 5.00 mmol), and p-tolueneboronic acid (0.748 g, 5.50 mmol) were taken up in 14 ml of dry dioxane under nitrogen and a 0.1 mol % aliquot from the catalyst solution (in dioxane) was added. The mixture was then heated to 80° C. for 12 hours. The mixture was then cooled to room temperature, diluted with Et2O, and extracted with a saturated NH4Cl solution (3×20 ml). The Et2O layer was dried over MgSO4, filtered and concentrated to give a viscous oil which was purified by flash chromatography to give 844 mg of 2-cyano-4'-methylbiphenyl in 87% isolated yield.
Workup
- customto form a catalyst solution that
- temperatureThe mixture was then heated to 80° C. for 12 hours
- temperatureThe mixture was then cooled to room temperature
- extractionextracted with a saturated NH4Cl solution (3×20 ml)
- dry with materialThe Et2O layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto give a viscous oil which
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-52f33d8eddfc4c1e80a15a682d9edf6a
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124476
Reaction notes
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