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

HRID 1446368노트

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HRID 1446368 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3f190937dfa94930a41805875a4e5bd3
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667064B2

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