Tetrahydrofuran → 9-(4-Methylphenyl)anthracene

HRID 600153Notes

Reaction equation

HRID 600153 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.B(O)(O)[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].C1COCC1>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.B(O)(O)C1C=CC(C)=CC=1.O>[C:20]1([CH3:23])[CH:21]=[CH:22][C:17]([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:18][CH:19]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 740629-BromoanthraceneHCID 79799Tolylboronic acid

Product 1

HCID 2643999-(4-Methylphenyl)anthraceneYield 107.5%

Reagents, catalysts & solvents 3

HCID 79799Tolylboronic acidCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

5 g (1 eq, 15.6 mmol) of 9-bromo anthracene, 3.61 g of p-tolylboronic acid (1.7 eq, 26.5 mmol), 2.15 g (1.3 eq, 20.3 mmol) of Na2CO3, and 0.54 g (0.03 eq, 0.47 mmol) of tetrakis(triphenylphosphine)palladium were put into a 500-ml round-bottomed flask in Ar gas condition. 5 ml of THF and 2.2 ml of water, based on 1 mmol of p-tolylboronic acid, were added into the flask and refluxed at 85° C. for 16 hours. After the color of the solution changed to dark brown, water was added to the solution, and the organic phase was extracted using ethyl acetate. The extracted organic phase was dried using anhydrous magnesium sulfate and filtered to remove the solvent. The dried organic phase was dissolved in a small amount of toluene and separated using column chromatography (silica and hexane). A resulting solid was recrystallized using toluene and methanol to obtain 4.5 g (86%) of a white solid.

Workup

  1. additionwere added into the flask
  2. additionwas added to the solution
  3. extractionthe organic phase was extracted
  4. customThe extracted organic phase was dried
  5. filtrationfiltered
  6. customto remove the solvent
  7. dissolutionThe dried organic phase was dissolved in a small amount of toluene
  8. customseparated
  9. customA resulting solid was recrystallized

Sources & evidence

ORD record
ord-86e36f830a8e4266bec3e881714b5477
Source dataset
uspto-grants-2011_03
Patent number
US07901793B2

Reaction notes

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