2-Bromo-4,6-dimethylaniline → N-(2-Bromo-4,6-dimethylphenyl)(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

HRID 1446368Notes

Reaction equation

HRID 1446368 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[Li]CCCC.Cl[Si:17]([CH3:28])([CH3:27])[CH:18]1[C:22]([CH3:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]1[CH3:26]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH:4][Si:17]([CH3:27])([CH3:28])[CH:18]1[C:22]([CH3:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]1[CH3:26]

Participants

5

Reactant 3

HCID 1705792-Bromo-4,6-dimethylanilineHCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 178418339Butyllithium

Product 1

HCID 58897749N-(2-Bromo-4,6-dimethylphenyl)(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, to a solution of 13.9 g (69.5 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 27.9 ml of 2.5 M (69.5 mmol) nBuLi in hexanes were added at −50° C. This mixture was stirred for 2 hours at ambient temperature. The resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 15.0 g (69.5 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane in 100 ml of THF at 0° C. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue 100 ml of toluene were added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 180-184° C./0.5 mm Hg. Yield 20.1 g (77%).

Workup

  1. additionThe resulting solution was added dropwise over ca. 1 hour
  2. stirringThe resulting mixture was stirred overnight at ambient temperature
  3. customevaporated to dryness
  4. additionTo the residue 100 ml of toluene were added
  5. filtrationThis mixture was filtered through a glass frit (G4)
  6. customThe filtrate was evaporated to dryness
  7. distillationFractional distillation
  8. customgave a yellow liquid, bp 180-184° C./0.5 mm Hg

Sources & evidence

ORD record
ord-3f190937dfa94930a41805875a4e5bd3
Source dataset
uspto-grants-2010_02
Patent number
US07667064B2

Reaction notes

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