Dichlorodiphenylsilane → 9-(CHLORODIPHENYLSILYL)-9H-FLUORENE

HRID 1699509Notes

Reaction equation

HRID 1699509 reaction equation
FF.[CH2:3]([CH2:6]OC)OC.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[C:14]1([Si:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([Cl:22])Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.CCCCCCC>[Cl:22][Si:20]([C:6]1[CH:3]=[CH:16][CH:15]=[CH:14][CH:19]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:14]1[C:16]2[CH:15]=[CH:28][CH:23]=[CH:24][C:17]=2[C:18]2[C:19]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

7

Reactant 4

HCID 6627DichlorodiphenylsilaneHCID 80711,2-DimethoxyethaneHCID 24524FluorineHCID 178418339Butyllithium

Product 1

HCID 27630639-(CHLORODIPHENYLSILYL)-9H-FLUORENEYield 66%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent2×

Conditions

Temperature
50 °C

Procedure

80 g (0.48 mol) of fluorine and 160 ml of toluene/12.8 ml (0.12 mol) of dimethoxyethane (DME) were placed in a reaction vessel and admixed with 182 ml (0.48 mo) of a 20% strength solution of butyllithium in toluene. The suspension was stirred for another 2 hours at 50° C. The suspension was diluted with 400 ml of heptane, cooled to −30° C. and added to a solution, cooled to −30° C., of 182 g (0.72 mol) of diphenyldichlorosilane in 400 ml of heptane. After stirring for 1.5 hours at room temperature, the suspension was heated to 60° C. and the lithium chloride was filtered off. After removal of the solvent, the solid which precipitated was suspended in heptane, filtered off, washed with heptane until virtually colorless and dried under reduced pressure. 123 g (66%) of 2a were obtained.

Workup

  1. temperaturecooled to −30° C.
  2. additionadded to a solution
  3. stirringAfter stirring for 1.5 hours at room temperature
  4. temperaturethe suspension was heated to 60° C.
  5. filtrationthe lithium chloride was filtered off
  6. customAfter removal of the solvent
  7. customthe solid which precipitated
  8. filtrationfiltered off
  9. washwashed with heptane until virtually colorless and
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f99baccfc4d14e149224797d041678e3
Source dataset
uspto-grants-2002_02
Patent number
US06346635B1

Reaction notes

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