Aniline → 4-(1-Bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline
Reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+].[Br:21][C:22]([F:31])([F:30])[C:23](Br)([F:28])[C:24]([F:27])([F:26])[F:25].C(=O)([O-])[O-].[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.COC(C)(C)C.O>[Br:21][C:22]([F:31])([F:30])[C:23]([C:13]1[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=1)([F:28])[C:24]([F:27])([F:26])[F:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
First 476.74 g (2.74 mol) of sodium dithionite and then 250 g (2.68 mol) of aniline were added at room temperature to a mixture of 4000 ml of water, 1200 ml of tert-butyl methyl ether, 270.61 g (3.22 mol) of sodium hydrogencarbonate and 10.94 g of tetra-n-butylammonium hydrogensulphate. Subsequently, a solution of 998.07 g of 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane in 300 ml of tert-butyl methyl ether was added dropwise at 35–40° C. and, on completion of addition, the mixture was stirred at RT for a further 18 h. If necessary, sodium carbonate was used to adjust to a pH of 5 and the organic phase was removed, dried and concentrated. The remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.
Workup
- customthe organic phase was removed
- customdried
- concentrationconcentrated
- distillationThe remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.
Sources & evidence
- ORD record
- ord-60d181a79ca94b06aeedf8f6463f5cf7
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041852B2
Reaction notes
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