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Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane → N-(4-Bromo-2,6-diisopropylphenyl)(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

HRID 1446362
Notes
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Reaction equation

HRID 1446362 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[Li]CCCC.Cl[Si:21]([CH3:32])([CH3:31])[CH:22]1[C:26]([CH3:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]1[CH3:30]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[C:5]([NH:6][Si:21]([CH3:31])([CH3:32])[CH:22]2[C:26]([CH3:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]2[CH3:30])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 117801144-Bromo-2,6-diisopropylanilineHCID 178418339Butyllithium

Product 1

HCID 58897738N-(4-Bromo-2,6-diisopropylphenyl)(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

Under an argon atmosphere, to a solution of 13.8 g (53 mmol) of 4-bromo-2,6-diisopropylaniline in 170 ml of THF, 21.0 ml of 2.5 M (53 mmol) of nBuLi in hexanes were added dropwise at −80° C. This mixture was additionally stirred for 30 minutes at ambient temperature and then added to a solution of 11.4 g (53 nimol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane in 70 ml of THF. The resulting mixture was stirred overnight and then evaporated to dryness. The residue was suspended in 100 ml of toluene. This suspension was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow oil, b.p. 156-162° C./0.15 mm Hg. Yield 12.8 g (55%).

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. customevaporated to dryness
  3. filtrationThis suspension was filtered through a glass frit (G4)
  4. customThe filtrate was evaporated to dryness
  5. distillationFractional distillation
  6. customgave a yellow oil, b.p. 156-162° C./0.15 mm Hg

Sources & evidence

ORD record
ord-7b7068abfc444bd6a8711119d8d0a200
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07667064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes