3,5-difluoro-4-(1-methoxy-2-methylpropan-2-yl)-N,N-bis(4-methoxybenzyl)aniline → 3,5-Difluoro-4-(1-methoxy-2-methylpropan-2-yl)aniline
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([F:33])[C:26]=1[C:27]([CH3:32])([CH3:31])[CH2:28][O:29][CH3:30])[N:5](CC1C=CC(OC)=CC=1)CC1C=CC(OC)=CC=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([F:33])[C:26]=1[C:27]([CH3:31])([CH3:32])[CH2:28][O:29][CH3:30])[NH2:5]Participants
3
Procedure
A solution of 3,5-difluoro-4-(1-methoxy-2-methylpropan-2-yl)-N,N-bis(4-methoxybenzyl)aniline (1 g, 2.20 mmol) in TFA (10 mL) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and to the obtained residue was added ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give 3,5-difluoro-4-(1-methoxy-2-methylpropan-2-yl)aniline (0.470 g, 2.184 mmol, 99%) as a pale-yellow oil.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionto the obtained residue was added ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-44b27219ef9e41cdba2590befdfa45f9
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
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