Hydrochloric Acid → Fluorene

HRID 2352750Notes

Reaction equation

HRID 2352750 reaction equation
C[C:2]1(C)[C:14]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](B(O)O)=[CH:6][CH:7]=2.IC1C=CC2C3C(=CC(I)=CC=3)C(C)(C)C=2C=1.C([O-])([O-])=O.[Na+].[Na+].Cl>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.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:4]1[C:3]2[CH2:2][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 129942022,7-Diiodo-9,9-dimethyl-9H-fluorene2×HCID 24820467(9,9-Dimethyl-9H-fluorene-2,7-diyl)diboronic acid2×

Product 1

HCID 6853Fluorene

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

With 9,9-dimethylfluorene-2,7-diboronic acid and 2,7-diiodo-9,9-dimethyl fluorene, which are synthesized according to synthesis example 1, a Suzuki reaction is carried out. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (1.0 mmol) is dissolved in THF (50 ml), followed by adding thereto 2,7-diiodo-9,9-dimethyl fluorene (50 mmol), a solution of 2M Na2CO3 (50 ml) and 9,9-dimethylfluorene-2,7-diboronic acid (25 mmol)/THF (100 ml) in this order. Thereafter, after refluxing for 7 hr, a reaction is brought to an end. The solution is cooled to room temperature, followed by substituting with toluene and adding substantially 30 ml of 1N HCl, further followed by washing a toluene phase with water until neutrality is obtained. After drying with sodium sulfate, followed by filtering and distilling the solvent away, and thereby a crude product is obtained. After washing with substantially 100 ml of methanol, a colorless crystal is obtained. Furthermore, by passing through a short column from hexane/ethyl acetate to remove original components, finally followed by recrystallizing, and thereby fluorene trimer (20 mmol) is obtained.

Workup

  1. customaccording to synthesis example 1
  2. customa Suzuki reaction
  3. additionby adding
  4. temperatureThereafter, after refluxing for 7 hr
  5. washby washing a toluene phase with water until neutrality
  6. customis obtained
  7. dry with materialAfter drying with sodium sulfate
  8. filtrationby filtering
  9. distillationdistilling the solvent away
  10. customa crude product is obtained
  11. washAfter washing with substantially 100 ml of methanol
  12. customa colorless crystal is obtained
  13. customto remove original components
  14. customby recrystallizing

Sources & evidence

ORD record
ord-c9fe9cd5547948c48f27a6922e597452
Source dataset
uspto-grants-2010_07
Patent number
US07749618B2

Reaction notes

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