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Chloride → 11-(Trimethylsilyl)undecyl bromide

HRID 652014
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HRID 652014 반응식
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Br.C[Si](C)(C)CCCBr.[Mg].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.[Cl-].[Li+].[Cl-]>O1CCCC1.CCOCC>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19]
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참가 물질

9

반응물 6

HCID 312ChlorideHCID 783101,8-DibromooctaneHCID 433294Lithium ChlorideHCID 5462224MagnesiumHCID 128458003-BromopropyltrimethylsilaneHCID 178504203HCID 178504203, 화합물

생성물 1

HCID 2019823411-(Trimethylsilyl)undecyl bromide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

The 3-(trimethylsilyl)propyl magnesium bromide prepared from 40 g. 3-(trimethylsilyl)propyl bromide and 5.1 g. magnesium turnings in 150 ml. dry ether was dropwise added to a cole (-20°) solution of 42 g. 1,8-dibromooctane, 170 mg. lithium chloride, and 270 mg. cuprus chloride in 120 ml. dry tetrahydrofuran under an argon atmosphere. When addition of the Grignard reagent was complete, the reaction was warmed to room temperature and stirring was continued for 17 hr. The solution was treated with 200 ml. 10% hydrochloric acid, the layers were separated, and the aqueous phase was washed twice with 100 ml. portions of ether. The combined organic phases were washed with brine, dried with anhydrous magnesium sulfate, and evaporated to a colorless liquid. Distillation of the crude product yielded the title compound.

후처리

  1. additionThe solution was treated with 200 ml
  2. custom10% hydrochloric acid, the layers were separated
  3. washthe aqueous phase was washed twice with 100 ml
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customevaporated to a colorless liquid
  7. distillationDistillation of the crude product

출처 및 근거

ORD 기록
ord-b4fd7ad7f4f84273ad34d7234b595888
출처 데이터셋
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04670421

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