1-Bromo-4-fluorobenzene → (2,4-Dimethylphenyl)(4-fluorophenyl)methanol
Reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH3:10][C:11]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].[Cl-].[NH4+]>C1COCC1.II>[CH3:10][C:11]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:12]=1[CH:13]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)[OH:14]Participants
Conditions
- Temperature
- 30 °C
Procedure
Under a nitrogen atmosphere, turnings of magnesium (16.8 g) were dispersed in THF (54 ml), and iodine (0.1 g) was added. Under a nitrogen atmosphere, a solution of 4-bromofluorobenzene (116 g) in THF (201 ml) was added dropwise at 15-40° C., and the mixture was stirred at 20-40° C. for 2 hr. The obtained mixture with a Grignard reagent was cooled and thereto was added dropwise a solution of 2,4-dimethylbenzaldehyde (81 g) in THF (81 ml) at 0-20° C. After the dropwise addition, the reaction mixture was stirred at 0-20° C. for 2 hr. A saturated aqueous ammonium chloride solution was added to stop the reaction. The reaction mixture was partitioned and the obtained organic layer was washed with saturated brine. The solvent was evaporated from the organic layer under reduced pressure to give (2,4-dimethylphenyl)-(4′-fluorophenyl)methanol (139.2 g, 100%) as a colorless oil. The obtained colorless oil was measured for 1H-NMR and found to be the same as in Example 1.
Workup
- additionAfter the dropwise addition
- stirringthe reaction mixture was stirred at 0-20° C. for 2 hr
- customthe reaction
- customThe reaction mixture was partitioned
- washthe obtained organic layer was washed with saturated brine
- customThe solvent was evaporated from the organic layer under reduced pressure
Sources & evidence
- ORD record
- ord-a86d16d1d8664f7693ec19d83d0270ac
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458975B1
Reaction notes
Loading…