Dimethylformamide → 5-Bromo-2-fluoro-3-methylbenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:20]=[O:21].C(OCC)(=O)C>C1COCC1.C(=O)=O.CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[C:4]([CH:3]=1)[CH:20]=[O:21]Participants
Procedure
To a solution of 5-bromo-2-fluorotoluene 169 (1.0 g, 5.29 mmol.) in anhydrous THF (4 mL) cooled in dry ice/acetone bath was added a 2 M solution of lithium diisopropylamide (2.6 mL, 5.2 mmol.). The reaction mixture was stirred for 1 hour in the dry ice/acetone bath. Anhydrous dimethylformamide (0.46 g, 6.35 mmol.) was added in a dropwise manner. The reaction mixture was allowed to warm to room temperature in 3 hours. Ethyl acetate (100 mL) was added. The organic layer was washed with 1 N hydrochloric acid, water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to afford 5-bromo-2-fluoro-3-methylbenzaldehyde 170 (1.08 g, 4.98 mmol.). The crude product was used in the next step without further purification.
Workup
- washThe organic layer was washed with 1 N hydrochloric acid, water and brine
- dry with materialThe organic layer was dried over sodium sulfate
- customThe organic solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-79114d9cd3ac4aaba7191445a2375469
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528132B2
Reaction notes
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