1,2-Dibromoethane → 1-Chloro-1,1,2,2-tetramethyl-2-(2-methyl-1H-inden-7-yl)disilane

HRID 557500

반응식

HRID 557500 반응식
[Mg].[CH3:2][C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2Br.BrCCBr.[Cl:17][Si:18]([CH3:24])([CH3:23])[Si:19](Cl)([CH3:21])[CH3:20]>C1COCC1.O>[Cl:17][Si:18]([CH3:24])([CH3:23])[Si:19]([CH3:21])([CH3:20])[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][C:3]([CH3:2])=[CH:11]2

참가 물질

7

반응물 4

HCID 78391,2-DibromoethaneHCID 780451,2-Dichloro-1,1,2,2-tetramethyldisilaneHCID 5462224MagnesiumHCID 121624797-Bromo-2-methyl-1H-indene

생성물 1

HCID 584187751-Chloro-1,1,2,2-tetramethyl-2-(2-methyl-1H-inden-7-yl)disilane

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To 7.97 g (0.332 mol) of magnesium turnings in 80 mL of THF a mixture of 33.4 g (0.160 mol) of 2-methyl-7-bromo-1H-indene, 30.0 g (0.160 mol) of 1,2-dibromoethane and 420 mL of THF was added dropwise with vigorous stirring at such rate that the mixture is refluxed. Further on, this mixture was additionally refluxed for 30 minutes. The obtained solution was added dropwise with vigorous stirring to a solution of 100 g (0.534 mol) of 1,2-dichloro-1,1,2,2-tetramethyldisilane in 100 mL of THF for 2 hours at room temperature (water bath cooling is required). The resulting mixture was stirred for 12 hours at ambient temperature and then evaporated to dryness. To the residue 100 mL of dry ether was added, and the obtained suspension was stirred for 20 minutes and then filtered through glass frit (G3). The precipitate was washed with 2×100 mL of ether. The combined filtrate was evaporated to dryness, the residue was dried and then rectificated in vacuum, b.p. 140° C.-145° C./1 mm Hg. Yield 26.3 g (58%) of the title product. 1H NMR (CD2Cl2): δ 7.22-7.32 (m, 3H, 4,5,6-H), 6.54 (m, 1H, 3-H), 3.39 (s, 2H, 1,1′-H), 2.21 (s, 3H, 2-Me), 0.66 (m, 3H, SiMe), 0.61 (m, 3H, SiMe), 0.59 (m, 3H, SiMe), 0.50 (m, 3H, SiMe). Anal. Calc. for C14H21ClSi2: C, 59.85; H, 7.53%. Found: C, 59.65; H, 7.72%.

후처리

  1. additionwas added dropwise
  2. temperatureis refluxed
  3. temperatureFurther on, this mixture was additionally refluxed for 30 minutes
  4. additionThe obtained solution was added dropwise
  5. stirringThe resulting mixture was stirred for 12 hours at ambient temperature
  6. customevaporated to dryness
  7. additionTo the residue 100 mL of dry ether was added
  8. stirringthe obtained suspension was stirred for 20 minutes
  9. filtrationfiltered through glass frit (G3)
  10. washThe precipitate was washed with 2×100 mL of ether
  11. customThe combined filtrate was evaporated to dryness
  12. customthe residue was dried

출처 및 근거

ORD 기록
ord-1d197302ba154412aa996447a697815e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058461B2

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