Potassium Carbonate → 9-(4'-Bromobiphenyl-4-yl)-10-phenylanthracene

HRID 2361203Notes

Reaction equation

HRID 2361203 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]([C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)=[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:29]2[CH:34]=[CH:33][C:32]([C:2]3[C:3]4[C:8]([C:9]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[C:10]5[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]5)=[CH:7][CH:6]=[CH:5][CH:4]=4)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 38416074'-Bromo-4-biphenylboronic Acid (contains varying amounts of Anhydride)HCID 149583739-Iodo-10-phenylanthracene

Product 1

HCID 588506609-(4'-Bromobiphenyl-4-yl)-10-phenylanthraceneYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene, 542 mg (2.70 mmol) of 4-(4-bromophenyl)phenylboronic acid, 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium, 3 mL (6 mmol) of potassium carbonate solution (2.0 mol/L), and 10 mL of toluene were stirred for 9 hours at 80° C. After reaction, toluene was added, and it was filtered through florisil®, celite, and alumina. The filtrate was washed with water and saturated saline, and then dried with magnesium sulfate. After natural filtering, the filtrate was concentrated, and when recrystallization was performed with a mixture of chloroform and hexane, 562 mg of 9-[4-(4-bromophenyl)phenyl]-10-phenylanthracene (PBA) that was a target substance and was a light brown solid was obtained in a yield of 45% (Synthesis Scheme (e-2)).

Workup

  1. additionwas added
  2. filtrationit was filtered through florisil®, celite, and alumina
  3. washThe filtrate was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationAfter natural filtering, the filtrate was concentrated
  6. customwhen recrystallization
  7. additionwas performed with a mixture of chloroform and hexane, 562 mg of 9-[4-(4-bromophenyl)phenyl]-10-phenylanthracene (PBA) that
  8. customwas obtained in a yield of 45% (Synthesis Scheme (e-2))

Sources & evidence

ORD record
ord-a211971aa32b4bf998cfa3026b7a5dd4
Source dataset
uspto-grants-2014_04
Patent number
US08686628B2

Reaction notes

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