Water → Anthracene

HRID 1094921Notes

Reaction equation

HRID 1094921 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1>[CH:6]1[C:5]2[C:10](=[CH:1][C:2]3[C:3]([CH:4]=2)=[CH:3][CH:2]=[CH:1][CH:10]=3)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 8418AnthraceneYield 456.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The resultant compound was dissolved in toluene (1 L) under a nitrogen atmosphere, and 2-naphthalenyl boronic acid (51.6 g, 0.3 mol), tetrakistriphenylphosphine palladium (9.3 g, 8.1 mmol), sodium carbonate (31.4 g, 0.3 mol), and water (300 ml) were added thereto. The reaction mixture was stirred under reflux for three hours. The reaction solution was cooled to about 60° C., filtered on silica gel, and extracted with toluene. The extracted solution was concentrated to remove an organic solvent, and methanol was added thereto. The resultant solid was filtered. The resultant yellowish brown matter was dissolved in methylene chloride, and methanol was dropwise added thereto to give an anthracene derivative (Cpd 1, 122 g, yield 85%) as a pale yellow solid.

Workup

  1. temperatureunder reflux for three hours
  2. filtrationfiltered on silica gel
  3. extractionextracted with toluene
  4. concentrationThe extracted solution was concentrated
  5. customto remove an organic solvent, and methanol
  6. additionwas added
  7. filtrationThe resultant solid was filtered
  8. dissolutionThe resultant yellowish brown matter was dissolved in methylene chloride
  9. additionmethanol was dropwise added

Sources & evidence

ORD record
ord-c878800336524d1e8de026f1631e48cf
Source dataset
uspto-grants-2012_03
Patent number
US08134035B2

Reaction notes

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