Sodium Chloride → 2,7-Diphenyl-9H-fluorene

HRID 661768Notes

Reaction equation

HRID 661768 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Ba+2].[OH-].[Cl-].[Na+]>C1(C)C=CC=CC=1.O.O1CCOCC1>[C:16]1([C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([C:2]5[CH:14]=[CH:13][CH:12]=[CH:4][CH:3]=5)=[CH:9][CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 66827Phenylboronic AcidHCID 1400732,7-DibromofluoreneHCID 6093286Barium hydroxide

Product 1

HCID 156468892,7-Diphenyl-9H-fluoreneYield 161.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

There were mixed 10.00 g (30.86 mmol) of 2,7-dibromofluorene, 15.05 g (123.45 mmol) of phenylboronic acid, 29.21 g (92.59 mmol) of barium hydroxide (Ba(OH)2.8H2O) and 0.71 g (0.62 mmol) of tetrakis(priphenylphosphine) palladium in an atmosphere of nitrogen. To the mixture, 200 mL of 1,4-dioxane and 33 mL of water were added at a room temperature. Temperature of the resultant mixture was raised up to 80° C., and the mixture was heated at 80° C. for 6 hours. Temperature of the mixture was cooled down to a room temperature, and 200 mL of toluene and 100 mL of a saturated solution of sodium chloride were added to the mixture. The obtained mixture was filtered, thereby obtaining a white solid. There was extracted 2,7-diphenyfluorene from the white solid with each 400 mL of hot THF three times. THF contained in the extract was distilled away, and the resultant solid was dried under a reduced pressure, thereby obtaining 7.94 g (yield: 80%) of 2,7-diphenyfluorene as a white solid.

Workup

  1. temperatureTemperature of the mixture was cooled down to a room temperature
  2. filtrationThe obtained mixture was filtered
  3. customobtaining a white solid
  4. extractionThere was extracted 2,7-diphenyfluorene from the white solid with each 400 mL of hot THF three times
  5. distillationwas distilled away
  6. customthe resultant solid was dried under a reduced pressure

Sources & evidence

ORD record
ord-8f637db2a7d74c4e8d8eb0dac6d0c130
Source dataset
uspto-grants-2011_12
Patent number
US08084559B2

Reaction notes

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