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

HRID 2361200Notes

Reaction equation

HRID 2361200 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-phenylanthracene

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 (abbreviation: Pd(PPh3)4 ), 3 mL (6 mmol) of potassium carbonate solution (2 mol/L), and 10 mL of toluene was stirred for 9 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 a mixed solution was naturally filtered and a filtrate was concentrated, an obtained solid was recrystallized with a mixture of chloroform and hexane. Then, 562 mg of 9-phenyl-10-(4-bromophenyl)anthracene (PA) that was a target substance and was a light brown solid was obtained in 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 a mixed solution was naturally filtered
  6. concentrationa filtrate was concentrated
  7. customan obtained solid was recrystallized with a mixture of chloroform and hexane
  8. customwas obtained in a yield of 45% (Synthesis Scheme (b-4))

Sources & evidence

ORD record
ord-5ec7bd71b6014c688fe4029882d3fa7c
Source dataset
uspto-grants-2014_04
Patent number
US08686628B2

Reaction notes

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