2,7-Di-tert-butylfluorene → HCID 178506710, compound

HRID 1892069Notes

Reaction equation

HRID 1892069 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li:26])CCC>CCOCC>[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[C:6]=1[Li:26])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 40900822,7-Di-tert-butylfluoreneHCID 178418339Butyllithium2×

Product 1

HCID 178506710HCID 178506710, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

A one-liter flask is charged with 2,7-di-tert-butylfluorene (50 g, 179.6 mmol) and a stir bar, capped with a rubber septum, and placed under a nitrogen atmosphere. Diethyl ether (about 300 mL) is added via a cannula, and the resulting mixture is cooled to −78° C. in a dry-ice bath. This mixture is stirred at this temperature as n-butyllithium (21.5 mL of 10 M in hexanes, 215 mmol) is added slowly via syringe. After the addition of n-butyllithium is complete, the reddish solution is slowly warmed to room temperature and stirred overnight (at least about 12 hours), to provide an ether solution of 2,7-di-tert-butylfluorenyl lithium.

Workup

  1. customcapped with a rubber septum
  2. additionis added slowly via syringe
  3. temperaturethe reddish solution is slowly warmed to room temperature

Sources & evidence

ORD record
ord-1dcf720aeccf43668c91b32f5a40e89b
Source dataset
uspto-grants-2013_08
Patent number
US08507621B2

Reaction notes

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