Ammonium Chloride → 1-(2,7-Di-t-butyl-9-fluorenyl)-2-(2-methyl-1-indenyl)ethylene

HRID 379337Notes

Reaction equation

HRID 379337 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])CCC.Br[CH2:28][CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][C:31]=1[CH3:39].[Cl-].[NH4+]>CCOCC.CCCCCC>[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)[CH:8]([CH:28]=[CH:29][CH:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[C:31]3[CH3:39])[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 40900822,7-Di-tert-butylfluoreneHCID 216979183-(2-Bromoethyl)-2-methylindeneHCID 178418339Butyllithium

Product 1

HCID 537146831-(2,7-Di-t-butyl-9-fluorenyl)-2-(2-methyl-1-indenyl)ethyleneYield 93.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To a 100 ml four-necked flask equipped with a reflux tube, a thermometer and a dropping funnel, 2,7-di-t-butylfluorene (1.18 g, 4.22 mmol) and dehydrated ether (30 ml) were introduced. To the flask was dropwise added a hexane solution of n-butyllithium (1.67 mol/l, 2.8 ml, 4.64 mmol) at 0° C. over a period of 1 hour, followed by stirring at room temperature for 7 hours. The reaction liquid became red orange transparent. Then, the liquid was cooled to −78° C. (a yellow orange slurry), to which a solution of 3-(2-bromoethyl)-2-methylindene (1 g, 4.22 mmol) in dehydrated ether (10 ml) was dropwise added over a period of 30 minutes. Then, the temperature of the system was allowed to spontaneously rise to room temperature, followed by stirring for 15 hours. The reaction mixture gradually became a yellow slurry. The resulting yellow slurry was poured into 200 ml of a saturated ammonium chloride aqueous solution to separate an ether phase. The aqueous phase was extracted with ether (100 ml×2), and a combined organic phase was dried over anhydrous magnesium sulfate, Then, the solvent was distilled off, and the resulting white yellow powder was reslurried with hexane (100 ml) and filtrated to obtain 1.70 g (yield: 93%) of an aimed product of a white powder.

Workup

  1. customTo a 100 ml four-necked flask equipped with a reflux tube
  2. customThe reaction liquid
  3. additionwas dropwise added over a period of 30 minutes
  4. customto spontaneously rise to room temperature
  5. stirringby stirring for 15 hours
  6. customto separate an ether phase
  7. extractionThe aqueous phase was extracted with ether (100 ml×2)
  8. dry with materiala combined organic phase was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. filtrationfiltrated

Sources & evidence

ORD record
ord-ba56b0c57cfb43bca89ab495eaf39292
Source dataset
uspto-grants-2001_10
Patent number
US06297333B1

Reaction notes

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