Potassium Fluoride → N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide

HRID 590914Notes

Reaction equation

Cl[C:2]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][CH:29]=[CH:28][C:3]=1[C:4]([NH:6][C:7]1[C:12]([Br:13])=[CH:11][C:10]([C:14]([F:26])([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=1[Br:27])=[O:5].[F-:35].[K+]>CS(C)=O>[Br:27][C:8]1[CH:9]=[C:10]([C:14]([F:26])([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[C:15]([F:18])([F:17])[F:16])[CH:11]=[C:12]([Br:13])[C:7]=1[NH:6][C:4](=[O:5])[C:3]1[CH:28]=[CH:29][CH:30]=[C:31]([N+:32]([O-:34])=[O:33])[C:2]=1[F:35]

Participants

Conditions

Temperature: 145 °C

Procedure

To 108 ml of DMSO were added 5.44 g (8.34 mmol) of 2-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide and 4.90 g (84.3 mmol) of potassium fluoride (spray-dried product), followed by stirring at 145° C. for 2 hours. The reaction solution was poured into ice-water to precipitate the crystal, and the obtained crystals were filtered and washed with hexane. The obtained crystals were purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=5:1) to prepare 2.42 g (yield 46%) of a target compound.

Workup

customto precipitate the crystal
filtrationthe obtained crystals were filtered
washwashed with hexane
customThe obtained crystals were purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-730e898f98d54014855a860178257e89
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09237745B2

Reaction notes

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