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

HRID 70565

反応式

HRID 70565 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-0119a32b104e4da9b9562b6b942d0ba1
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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