Potassium Carbonate → 4,4'-Difluorobenzophenone
Reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>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]>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[O:14])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
A schlenk tube containing the mixture of 4,4′-Diflourobenzhydrol (220 mg, 1.0 mmol), K2CO3 (276 mg, 2.0 mmol), Pd(dba)2 (6 mg, 10 μmol) and ligand 1 (10 mg, 30 μmol) was degassed thoroughly under vacuum and purged with Ar. Chlorobenzene (0.15 mL) and toluene (4 mL) were added to the schlenk. The mixture was heated at 105° C. for 12 h. The reaction was taken up in ether (100 mL) and washed with H2O (30 mL) and brine (30 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate as elute to afford compound A as an off-white solid (215 mg, 98%) after drying under vacuum.
Workup
- additionA schlenk tube containing
- customwas degassed thoroughly under vacuum
- custompurged with Ar
- additionChlorobenzene (0.15 mL) and toluene (4 mL) were added to the schlenk
- washwashed with H2O (30 mL) and brine (30 mL)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude product was purified by column chromatography on silica gel
- washas elute
Sources & evidence
- ORD record
- ord-716356e6eaf64f07b214a95527b48cbf
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350916B1
Reaction notes
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