Water → 2,7-Di-tert-butylfluorene

HRID 2253257Notes

Reaction equation

HRID 2253257 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=S)=S.[C:17](Cl)([CH3:20])([CH3:19])[CH3:18].O>CCCCCC>[C:17]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][C:2]([C:5]([CH3:6])([CH3:13])[CH3:4])=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 6853FluoreneHCID 10486tert-BUTYL CHLORIDE

Product 1

HCID 40900822,7-Di-tert-butylfluoreneYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Fluorene (30.4764 g, 183.5928 mmol), FeCl3 (0.5 eq., 14.7517 g) and CS2 (300 ml) were introduced to a three-neck 1 liter flask fitted with a mechanical stirrer and hydrogen chloride trap which had been flame-dried and filled with nitrogen, and stirred. t-BuCl (2.5 eq., 50 ml) was dripped into this solution during 10 minutes. The reaction solution was stirred at room temperature for 7 hours, then water was added to quench the reaction. Next, the organic layer was extracted twice with methylene chloride, the extracted organic layer was washed with saturated salt solution, and dried using MgSO4. The dried solution was filtered, and was concentrated under reduced pressure to give a crude product (49.4598 g, brown solid). This crude product was refined by silica gel column chromatography (hexane), and the target product 2,7-di-t-butylfluorene (43.6058 g, 85%, white solid) was thus obtained. For the reaction, no further purification was carried out, but for measurement of analysis data, a sample which had been recrystallized from EtOH was used.

Workup

  1. customfitted with a mechanical stirrer and hydrogen chloride trap which
  2. customhad been flame-dried
  3. additionfilled with nitrogen
  4. stirringThe reaction solution was stirred at room temperature for 7 hours
  5. customto quench
  6. customthe reaction
  7. extractionNext, the organic layer was extracted twice with methylene chloride
  8. washthe extracted organic layer was washed with saturated salt solution
  9. customdried
  10. filtrationThe dried solution was filtered
  11. concentrationwas concentrated under reduced pressure
  12. customto give a crude product (49.4598 g, brown solid)

Sources & evidence

ORD record
ord-8dc7ca9ecfac445bb32b4e94c8b0b806
Source dataset
uspto-grants-2008_01
Patent number
US07323538B2

Reaction notes

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