Sodium Carbonate → HCID 24744244, compound

HRID 735896Notes

Reaction equation

HRID 735896 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 24744244HCID 24744244, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22272177Toluene waterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of dibenzofuran-4-boronic acid (30 g, 0.14 mol), 4-bromonitrobenzene (25.7 g, 0.127 mol), sodium carbonate (150 g) in toluene/water (500 mL/500 mL) was added tetrakis(triphenylphosphine)palladium(0) (8.2 g, 0.7 mol %) and the resulting reaction mixture was refluxed for 20 h under N2 atmosphere. The toluene layer was separated and concentrated to 200 mL. The concentrated solution was cooled to 0° C. and filtered off. The collected solid was dried and dissolved in chloroform and the obtained solution was filtered through celite bed to remove insoluble materials. The filtrate was concentrated under vacuum to give the title compound (23 g, 58%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 20 h under N2 atmosphere
  3. customThe toluene layer was separated
  4. concentrationconcentrated to 200 mL
  5. filtrationfiltered off
  6. customThe collected solid was dried
  7. dissolutiondissolved in chloroform
  8. filtrationthe obtained solution was filtered through celite bed
  9. customto remove insoluble materials
  10. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ca999d04824049c6853ada4b925dfbbb
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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