Cesium carbonate → 4,4'-(4-Bromo-6-nitro-1,3-phenylene)bis(oxy)bis(1,3-difluorobenzene)

HRID 633525

Reaction equation

HRID 633525 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1F.[C:13](=[O:16])([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:27][C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[F:19])=[CH:4][C:3]=1[O:16][C:13]1[CH:22]=[CH:21][C:20]([F:19])=[CH:25][C:24]=1[F:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 2230781-Bromo-2,4-difluoro-5-nitrobenzene

Product 1

HCID 904167304,4'-(4-Bromo-6-nitro-1,3-phenylene)bis(oxy)bis(1,3-difluorobenzene)Yield 120.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-bromo-2,4-difluoro-5-nitrobenzene (0.3 g, 1.26 mmol) and cesium carbonate (0.86 g, 2.65 mmol) in DMSO (6.3 mL) was added dropwise 2,4-difluorophenol (0.27 g, 2.10 mmol). The mix was stirred for 60 minutes at ambient temperature and partitioned between ethyl acetate and water, adjusting the pH to 6 with HCl. The organic layer was washed with water, saturated aqueous sodium chloride, dried (MgSO4), filtered, and concentrated to afford the title compound (0.578 g, 100%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cfed1b56bb364f88bf20d91a422f550b
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Linked notes

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