Water → 2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoroprop-2-yl)-6-(difluoromethoxy)aniline

HRID 70809Notes

Reaction equation

[Br:1][C:2]([F:21])([F:20])[C:3]([C:9]1[CH:15]=[C:14]([O:16][CH:17]([F:19])[F:18])[C:12]([NH2:13])=[CH:11][CH:10]=1)([F:8])[C:4]([F:7])([F:6])[F:5].[Br:22]N1C(=O)CCC1=O.O.C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:22][C:11]1[CH:10]=[C:9]([C:3]([F:8])([C:4]([F:7])([F:6])[F:5])[C:2]([Br:1])([F:20])[F:21])[CH:15]=[C:14]([O:16][CH:17]([F:18])[F:19])[C:12]=1[NH2:13]

Participants

Conditions

Temperature: 70 °C

Procedure

4-(1-Bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline (810 mg) was dissolved in acetic acid, added with N-bromosuccinimide (390 mg), and stirred at 70° C. for 3 hours. Water was added to the reaction solution and extraction was carried out twice using ethyl acetate. The organic phases were combined and neutralized with sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was removed by distillation under the reduced pressure. The resulting residues were purified by column chromatography to obtain 2-bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoroprop-2-yl)-6-(difluoromethoxy)aniline (730 mg, 75%).

Workup

dry with materialdried over anhydrous magnesium sulfate
filtrationThe drying agent was filtered off
customthe solvent was removed by distillation under the reduced pressure
customThe resulting residues were purified by column chromatography

Sources & evidence

ORD record: ord-e91a105bc48d4e5cbfffa433993d5665
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822691B2

Reaction notes

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