Dimethylformamide → 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)acetamide
Reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:16].C[Li].[Li+].[Br-].[Li]C(CC)C.CN([CH:29]=[O:30])C>C1COCC1.CCOCC.C1CCCCC1>[F:12][C:11]([F:14])([F:13])[C:10]([NH:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH:29]=[O:30])=[C:3]([CH3:16])[CH:4]=1)=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
A solution of N-(4-bromo-3,5-dimethylphenyl)-2,2,2-trifluoroacetamide (14.0 g, 47.3 mmol) in THF (200 mL) was cooled to −78° C. Under a nitrogen atmosphere, methyllithium/LiBr (44.1 mL of a 1.5 M solution in Et2O, 66.2 mmol) was added slowly to the solution. After 5 min of stirring, sec-BuLi (47.3 mL of a 1.4 M solution in cyclohexane, 66.2 mmol) was added slowly to the reaction keeping the temperature at −78° C. After 5 min, anhydrous DMF (25.5 mL, 331 mmol) was added slowly to the solution. After the addition, the solution was warmed to 25° C. and after 30 min the reaction mixture was quenched with water. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure to give 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)-acetamide as a yellow solid.
Workup
- customat −78° C
- waitAfter 5 min
- additionAfter the addition
- customwas quenched with water
- extractionThe aqueous layer was extracted with CH2Cl2
- washthe combined organic layers were washed with water, brine
- dry with materialdried with MgSO4
- filtrationfiltered
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-8af8b5fc928d45dfb98fdf63a3ce48cc
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222248B2
Reaction notes
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