Dichlorodimethylsilane → Chloro[6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl]dimethylsilane

HRID 716450Notes

Reaction equation

HRID 716450 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:12]=1[O:13][C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[F:24])[CH2:9][C:8]([CH3:31])=[CH:7]2)([CH3:3])[CH3:2].[H-].[K+].[Cl:34][Si:35](Cl)([CH3:37])[CH3:36]>C1COCC1>[Cl:34][Si:35]([CH:7]1[C:6]2[C:10](=[C:11]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:12]([O:13][C:14]3[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=3[F:24])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)[CH:9]=[C:8]1[CH3:31])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 82127Potassium hydrideHCID 893925075-isopropyl-2-methyl-6-(pentafluorophenoxy)-7-phenyl-1H-indene

Product 1

HCID 89392521Chloro[6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl]dimethylsilaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.61 g (20.0 mmol) of 5-isopropyl-2-methyl-6-(pentafluorophenoxy)-7-phenyl-1H-indene in 200 ml of THF cooled to −25° C., 885 mg (22.1 mmol) of potassium hydride was added. The resulting mixture was stirred overnight at room temperature, filtered through glass frit (G3) to remove an excess of KH, then cooled to −25° C., and 13.0 g (101 mmol, 5 eq.) of dichlorodimethylsilane was added in one portion. The resulting solution was stirred overnight at room temperature, then evaporated to dryness. The residue was dissolved in 200 ml of toluene, and the formed suspension was filtered through glass frit (G3). The precipitate was additionally washed by 2×30 ml of toluene. The combined filtrate was evaporated to dryness to give 10.5 g (99%) of the title product which was further used without an additional purification.

Workup

  1. filtrationfiltered through glass frit (G3)
  2. customto remove an excess of KH
  3. temperaturecooled to −25° C.
  4. stirringThe resulting solution was stirred overnight at room temperature
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in 200 ml of toluene
  7. filtrationthe formed suspension was filtered through glass frit (G3)
  8. washThe precipitate was additionally washed by 2×30 ml of toluene
  9. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-484434080e6f45068d5d251c2f84bef0
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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