1-Bromo-3-methylbutane → 1-Bromo-4-[(3-methylbutoxy)methyl]benzene

HRID 70565

반응식

HRID 70565 반응식
[H-].[Na+].Br[CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:15][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 701194-Bromobenzyl alcohol

생성물 1

HCID 584522841-Bromo-4-[(3-methylbutoxy)methyl]benzene수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (purity: 55%, 700 mg) and 1-bromo-3-methylbutane (2.56 mL) were added to a solution of 4-bromobenzylalcohol (2.0 g) in N,N-dimethylformamide (40 mL) under ice-cooling, and the mixture was stirred at room temperature for five hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→30:1) to give the title compound (2.31 g, 85%).

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→30:1)

출처 및 근거

ORD 기록
ord-0119a32b104e4da9b9562b6b942d0ba1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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