Water → 2-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide

HRID 2360368Notes

Reaction equation

CN1C(=O)N(C)CC1.[Br:9][C:10]1[CH:16]=[C:15]([C:17]([F:29])([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[C:18]([F:21])([F:20])[F:19])[CH:14]=[C:13]([Br:30])[C:11]=1[NH2:12].[Cl:31][C:32]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35].O>C(OCC)(=O)C>[Cl:31][C:32]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([NH:12][C:11]1[C:10]([Br:9])=[CH:16][C:15]([C:17]([F:29])([C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])[C:18]([F:19])([F:20])[F:21])=[CH:14][C:13]=1[Br:30])=[O:35]

Participants

Conditions

Temperature: 140 °C

Procedure

To 27 ml of DMI were added 9.90 g (21.1 mmol) of 2,6-dibromo-4-(perfluorobutan-2-yl)aniline and 4.60 g (20.9 mmol) of 2-chloro-3-nitrobenzoyl chloride, followed by stirring at 140° C. for 4 hours. To the reaction solution were added water and ethyl acetate, and the organic phase was extracted, and washed with 1 mol/L of an aqueous sodium hydroxide solution, saturated brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1→10:1→5:1→3:1) to prepare 5.44 g (yield 40%) of a target compound.

Workup

extractionthe organic phase was extracted
washwashed with 1 mol/L of an aqueous sodium hydroxide solution, saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThen, the solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1→10:1→5:1→3:1)

Sources & evidence

ORD record: ord-76f2f225bbf447b6b90cbc432347405e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686044B2

Reaction notes

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