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

HRID 658957Notes

Reaction equation

HRID 658957 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>[C:16]1([C:9]2[C:10]3[C:15]([C:2]([C:26]4[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=4)=[C:3]4[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=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 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene, 542 mg (2.70 mmol) of p-bromo phenylboronic acid, 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4), 3 mL (6 mmol) of potassium carbonate aqueous solution (2 mol/L), and 10 mL of toluene was stirred for nine hours at 80° C. After reaction, toluene was added and filtration was carried out using florisil, celite, and alumina. A filtrate was washed with water and saturated saline, and then dried with magnesium sulfate. After the mixture was subjected to natural filtration, the filtrate was concentrated, and when it was recrystallized with chloroform and hexane, 562 mg of 9-phenyl-10-(4-bromophenyl)anthracene that was a target substance is obtained as a light brown solid at a yield of 45% (Synthesis scheme (b-4)).

Workup

  1. additionwas added
  2. filtrationfiltration
  3. washA filtrate was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate
  5. filtrationAfter the mixture was subjected to natural filtration
  6. concentrationthe filtrate was concentrated
  7. customwhen it was recrystallized with chloroform and hexane, 562 mg of 9-phenyl-10-(4-bromophenyl)anthracene that
  8. customis obtained as a light brown solid at a yield of 45% (Synthesis scheme (b-4))

Sources & evidence

ORD record
ord-5c8a0b25fef149d0ab4f9a205b353216
Source dataset
uspto-grants-2011_12
Patent number
US08076676B2

Reaction notes

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