Fluorene → HCID 67259085, compound

HRID 2425307Notes

Reaction equation

HRID 2425307 reaction equation
[Li]CCCC.CCCCCC.[CH:12]1[C:24]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.Cl[Si:26]([CH:29]1[C:37]2[C:32](=[C:33]([CH3:39])[CH:34]=[C:35]([CH3:38])[CH:36]=2)[CH:31]=[C:30]1[CH3:40])([CH3:28])[CH3:27].[Li]>CCOCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:40][C:30]1[CH:29]([Si:26]([CH:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:24]2=[CH:12][CH:13]=[CH:14][CH:15]=3)([CH3:28])[CH3:27])[C:37]2[C:32]([CH:31]=1)=[C:33]([CH3:39])[CH:34]=[C:35]([CH3:38])[CH:36]=2

Participants

9

Reactant 5

HCID 6853FluoreneHCID 8058HexaneHCID 3028194LithiumHCID 59735669HCID 59735669, compoundHCID 178418339Butyllithium

Product 1

HCID 67259085HCID 67259085, compoundYield 108.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2.5 M n-BuLi solution in hexane (16.75 mL, 41.88 mmol) was added dropwise at 0° C. under stirring to a solution of 6.63 g of fluorene (39.89 mmol) in 100 ml of Et2O in a 500 mL 3-necked round flask. The resulting orange solution was allowed to warm up to room temperature and stirred for 1.5 h. A solution of chloro(2,4,6-trimethyl-indenyl)dimethylsilane (10 g, 39.87 mmol) in 20 mL of THF was cooled to 0° C. and slowly added to the lithium salt solution, also previously cooled to 0° C. At the end of the addition a light brown suspension was obtained. The latter was allowed to warm up to room temperature and stirred for 1.5 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 150 mL of toluene and then filtered to remove LiCl. The filtrate was dried in vacuo to give 16.42 g of a brown oil, which resulted to be the expected ligand contaminated by minor amounts of non identified by-products (crude yield quantitative). The product was used as such in the next step without further purification.

Workup

  1. temperaturealso previously cooled to 0° C
  2. additionAt the end of the addition a light brown suspension
  3. customwas obtained
  4. temperatureto warm up to room temperature
  5. stirringstirred for 1.5 h
  6. customThen the reaction mixture was evaporated under reduced pressure
  7. customto give a brown sticky solid, which
  8. filtrationfiltered
  9. customto remove LiCl
  10. customThe filtrate was dried in vacuo

Sources & evidence

ORD record
ord-da257939f86b4d82ac9927cc3327c4c6
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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