Sodium Carbonate → 9-(4-Bromophenyl)phenanthrene

HRID 1429324Notes

Reaction equation

HRID 1429324 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 117757049-Phenanthracenylboronic acid

Product 1

HCID 231486109-(4-Bromophenyl)phenanthreneYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

In argon atmosphere, a mixture of 39.25 g (177 mmol) of 9-phenanthreneboronic acid, 50.0 g (177 mmol) of 4-bromoiodobenzene, 4.10 g (3.54 mmol) of tetrakis(triphenylphosphine)palladium (0), 400 ml of toluene, and 265 ml of a 2 M sodium carbonate aqueous solution was refluxed under stirring for 24 h. After the reaction, the reaction mixture was filtered and the aqueous phase was removed. The organic phase was washed with water and dried over magnesium sulfate, and then the toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 42.6 g (yield: 72%) of 9-(4-bromophenyl)phenanthrene.

Workup

  1. temperaturewas refluxed
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe aqueous phase was removed
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe toluene was removed by distillation under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c48fabceb60947fa81cd1c81ab67d355
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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