Sodium Chloride → 2-Bromo-1-(2,4-difluorophenoxy)-4-nitrobenzene

HRID 1487339Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[F:12]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Bromo-1-fluoro-4-nitrobenzene (15 g, 68.2 mmol), 2,4-difluorophenol (7.82 mL, 82 mmol), and cesium carbonate (26.7 g, 82 mmol) were combined in DMSO (75 mL), heated at 110° C. for 1 hour, and then cooled. To the cooled reaction mixture was added water (1000 mL) and saturated aqueous sodium chloride (1000 mL). The mixture was extracted with ethyl acetate (3×200 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered, and concentrated under reduced pressure to give a crude solid which was used in the next step without additional purification.

Workup

temperaturecooled
customTo the cooled reaction mixture
extractionThe mixture was extracted with ethyl acetate (3×200 mL)
washThe combined organics were washed with saturated aqueous sodium chloride
dry with materialdried (anhydrous magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a crude solid which
customwas used in the next step without additional purification

Sources & evidence

ORD record: ord-de216df35a7543ff9ad64d58062f1a33
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428514B2

Reaction notes

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