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

HRID 1446366Notes

Reaction equation

HRID 1446366 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[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])[C:5]([NH:6][Si:17]([CH3:27])([CH3:28])[CH:18]2[C:22]([CH3:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]2[CH3:26])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 905494-Bromo-2,6-xylidineHCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 178418339Butyllithium

Product 1

HCID 58897752N-(4-Bromo-2,6-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 11.2 g (55.9 mmol) of 4-bromo-2,6-dimethylaniline in 170 ml of THF, 22.4 ml of 2.5 M (55.9 mmol) nBuLi in hexanes were added at −80° C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 12.0 g (55.9 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane in 80 ml of THF. 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 170-175° C./0.6 mm Hg. The product crystallizes slowly at ambient temperature. Yield 8.45 g (40%).

Workup

  1. temperatureThis mixture was warmed for ca. 1 hour to ambient temperature
  2. additionThen, the resulting solution was added dropwise over ca. 1 hour
  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 170-175° C./0.6 mm Hg
  9. customThe product crystallizes slowly at ambient temperature

Sources & evidence

ORD record
ord-1b00b531abcf4f02a5790e6f55d2dfa0
Source dataset
uspto-grants-2010_02
Patent number
US07667064B2

Reaction notes

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