Dimethylformamide → 4-(Trifluoromethyl)pyridine-2-carbaldehyde
Reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C>CCOCC>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:20]=[O:21])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To 2-bromo-4-(trifluoromethyl)pyridine (700 mg, 3.1 mmol) in ether (30 ml) at −78° C., BuLi (1.6M in hexanes, 2.13 ml) was added. After 40 min, DMF (340 mg) was added and the reaction mixture was stirred at −78° C. for a further 45 minutes and the reaction mixture was allowed to come to rt over a period of 1 h. Then the reaction mixture was quenched with solid ammonium chloride and partitioned between water and ether. Organic layers were dried and evaporated to provide 4-(trifluoromethyl)picolinaldehyde as a crude residue which was carried to the next step without further purification.
Workup
- waitto come to rt over a period of 1 h
- customThen the reaction mixture was quenched with solid ammonium chloride
- custompartitioned between water and ether
- customOrganic layers were dried
- customevaporated
Sources & evidence
- ORD record
- ord-7e1bf1bd0fb64035859c6490de490d03
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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