Potassium Carbonate → 9-(4-Bromophenyl)-10-phenylanthracene

HRID 1639483Notes

Reaction equation

HRID 1639483 reaction equation
I[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Br:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>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:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:3]3[C:8]([C:9]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 149583739-Iodo-10-phenylanthracene

Product 1

HCID 221382759-(4-Bromophenyl)-10-phenylanthraceneYield 52%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Into a 50 mL three-neck flask were put 1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene and 542 mg (2.70 mmol) of p-bromophenyl boronic acid. The atmosphere in the flask was replaced with nitrogen. After that, 10 mL of toluene and 3 mL of potassium carbonate aqueous solution (2.0 M) were added to the flask. This mixture was degassed under reduced pressure, then 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. The mixture was stirred under a nitrogen stream at 80° C. for 9 hours. After the stirring, about 20 mL of toluene was added to this mixture. Then, the mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and a saturated saline, and then dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give a solid. The obtained solid was recrystallized with chloroform/hexane to give 0.56 g of a light-brown solid, which was the object of the synthesis, in a yield of 45%.

Workup

  1. customInto a 50 mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. filtrationThen, the mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  4. washThe obtained filtrate was washed with water
  5. dry with materiala saturated saline, and then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe obtained filtrate was concentrated
  8. customto give a solid
  9. customThe obtained solid was recrystallized with chloroform/hexane

Sources & evidence

ORD record
ord-e5b9ffe24bfb4755865481d8a016576f
Source dataset
uspto-grants-2012_02
Patent number
US08110122B2

Reaction notes

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