Dichloromethane → 2,6-Dichloro-4-(perfluoropropan-2-yl)aniline
Reaction equation
[F:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=C[CH:12]=1)([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].[Cl:18]N1C(=O)CCC1=O.Cl[CH2:27][Cl:28]>>[Cl:18][C:15]1[CH:16]=[C:11]([C:2]([F:1])([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4])[CH:12]=[C:27]([Cl:28])[C:14]=1[NH2:17]Participants
Procedure
To a solution of 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (10 g, 38.30 mmol) (prepared according to EP 1,006,102) in dichloromethane (150 ml), at 20° C., was added N-chlorosuccinimide (“NCS”) (21.48 g, 160.8 mmol). The reaction mixture was stirred overnight at ambient temperature. The reaction was quenched by addition of aqueous sodium hydroxide (2N) and the phases were separated. The aqueous layer was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4) to give 2,6-dichloro-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (7.6 g, 60.1% yield). 1H-NMR (CDCl3, 400 MHz): 7.41 (s, 2H), 4.77 (s, 2H) ppm.
Workup
- customThe reaction was quenched by addition of aqueous sodium hydroxide (2N)
- customthe phases were separated
- extractionThe aqueous layer was extracted with dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4)
Sources & evidence
- ORD record
- ord-49e3215bf91d41caad3a72540c371dd3
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389767B2
Reaction notes
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