Sodium Carbonate → 9-Phenylanthracene

HRID 1928967Notes

Reaction equation

HRID 1928967 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.COCCOC>[C:16]1([C:2]2[C:3]3[C:8]([CH:9]=[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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 740629-Bromoanthracene

Product 1

HCID 117669-PhenylanthraceneYield 98.3%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

25.7 g (100 mmol) of 9-bromoanthracene, 12.8 g (105 mmol) of phenylboronic acid, 233 mg (1.0 mmol) of palladium acetate(II), and 913 mg (3.0 mmol) of tri(o-tolyl)phospine were put into a 500-mL three-neck flask and nitrogen substitution was carried out. Then, 100 mL of ethylene glycol dimethyl ether and 75 mL (190 mmol) of a sodium carbonate aqueous solution (2.0 mol/L) were added thereto, and the reaction mixture was stirred at 90° C. for 5 hours. After the reaction, the reaction mixture was subjected to suction filtration to collect a precipitated solid. The obtained solid was dissolved into toluene, and the resulting solution was subjected to suction filtration through Florisil, celite, and then alumina. The filtrate was washed with water and saturated saline, and then an organic layer was dried with magnesium sulfate. This mixture is naturally filtrated, and the filtrate was condensed to obtain 25.0 g of a light-brown solid that was a target matter with the yield of 98%.

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was subjected to suction filtration
  3. customto collect a precipitated solid
  4. dissolutionThe obtained solid was dissolved into toluene
  5. filtrationthe resulting solution was subjected to suction filtration through Florisil, celite
  6. washThe filtrate was washed with water and saturated saline
  7. dry with materialan organic layer was dried with magnesium sulfate
  8. filtrationThis mixture is naturally filtrated
  9. customcondensed

Sources & evidence

ORD record
ord-a7ba63feac12441b876398d0b4384704
Source dataset
uspto-grants-2012_05
Patent number
US08183793B2

Reaction notes

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