Dimethylformamide → 5-Fluoro-2-methylbenzaldehyde
Reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([Li])CCC.CN(C)[CH:17]=[O:18]>O1CCCC1.CCCCCC>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([CH:7]=1)[CH:17]=[O:18]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-bromo-4-fluorotoluene (16.0 g) in anhydrous tetrahydrofuran was treated dropwise at −78° C. with a 1.6 M solution of butyllithium in hexane (55.5 ml). At the same temperature, the mixture was stirred and treated dropwise with a solution of dimethylformamide (6.8 g) in tetrahydrofuran (20 ml). After being allowed to warm to 0° C., the reaction mixture was combined with ice-water. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 5-fluoro-2-methylbenzaldehyde (11.5 g) as an oil.
Workup
- extractionThe reaction mixture was extracted with ethyl acetate
- washthe organic layer was washed successively with water and saturated brine
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-6b78eb3c3e5c4060a7cb232406f7f67d
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706732B1
Reaction notes
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