3,6-DI-Tert-butyl-2,7-bis(chloromethyl)-9H-fluorene → 2,7-Dimethyl-3,6-ditert-butyl-fluorene

HRID 10944Notes

Reaction equation

HRID 10944 reaction equation
Cl[CH2:2][C:3]1[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH2:24]Cl)=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:24][C:9]1[C:10]([C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:11][C:12]2[C:13]3[C:5](=[CH:4][C:3]([CH3:2])=[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:14]=3)[CH2:6][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 149482733,6-DI-Tert-butyl-2,7-bis(chloromethyl)-9H-fluoreneHCID 21226445Aluminium lithium hydride

Product 1

HCID 219826932,7-Dimethyl-3,6-ditert-butyl-fluoreneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,7-dichloromethyl-3,6-di-t-butylfluorene (0.75 g, 2.0 mmol) in THF (15 ml) was added a small portion of LiAlH4 (220 mg, 5.8 mmol) under stirring and the mixture was refluxed for 4 hours. The reaction was quenched with water and NaOH and extracted with ether. The ether solution was evaporated under vacuum to give a white solid of 2,7-di-methyl-3,6-di-tert-butyl-fluorene with a yield of 85%.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe reaction was quenched with water and NaOH
  3. extractionextracted with ether
  4. customThe ether solution was evaporated under vacuum

Sources & evidence

ORD record
ord-3c29fad66fc74395b988834494b86fcf
Source dataset
uspto-grants-2006_08
Patent number
US07094938B1

Reaction notes

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