4-Bromo-2,6-xylidine → N-(4-Bromo-2,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl) dimethylsilanamine

HRID 1922327

반응식

HRID 1922327 반응식
[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]([CH:20]1[C:24]2[S:25][CH:26]=[CH:27][C:23]=2[C:22]([CH3:28])=[C:21]1[CH3:29])([CH3:19])[CH3:18]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6][Si:17]([CH:20]2[C:24]3[S:25][CH:26]=[CH:27][C:23]=3[C:22]([CH3:28])=[C:21]2[CH3:29])([CH3:18])[CH3:19])=[C:4]([CH3:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 905494-Bromo-2,6-xylidineHCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 58526147N-(4-Bromo-2,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl) dimethylsilanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under an argon atmosphere, to a solution of 12.4 g (61.9 mmol) of 4-bromo-2,6-dimethylaniline in 300 ml of THF, 16.5 ml of 2.5 M (41.2 mmol) nBuLi in hexanes was added at −80° C. This mixture was warmed for ca. 2 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 10.0 g (41.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 50 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 154-156° C./0.05 mm Hg. The product crystallizes slowly at ambient temperature. Yield 8.36 g (50%).

후처리

  1. temperatureThis mixture was warmed for ca. 2 hour to ambient temperature
  2. additionThen, the resulting solution was added dropwise over ca. 1 hour
  3. customevaporated to dryness
  4. additionTo the residue, 150 ml of toluene was 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 154-156° C./0.05 mm Hg
  9. customThe product crystallizes slowly at ambient temperature

출처 및 근거

ORD 기록
ord-ca0df73610674f659fde1aa65bc9eeee
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173828B2

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