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

HRID 590913Notes

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-a3596cb98eb24f9eae17f4bcb146dbc0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09237745B2

Reaction notes

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