1-Bromo-2-methylpropane → 1-Bromo-4-(2-methylpropoxy)benzene

HRID 1515443ノート

反応式

HRID 1515443 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH:16]([CH3:18])[CH3:17]>CC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 65551-Bromo-2-methylpropaneHCID 78084-BromophenolHCID 11430Potassium Carbonate

生成物 1

HCID 153241111-Bromo-4-(2-methylpropoxy)benzene収率 60.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

4-Bromo-phenol (2 g, 11.6 mmol) is dissolved in acetone (40 mL). Potassium carbonate (8 g, 38.4 mmol) is then added followed by isobutyl bromide (4 g, 29.2 mmol). The reaction is heated to reflux for four days, refilling solvent as necessary. The reaction mixture is diluted with water and extracted with ether, the organic layer is separated and concentrated in vacuo. The residue is dissolved in hexane dried with magnesium sulfate, and filtered through a plug of silica gel. The solvent is removed in vacuo to afford 1.6 g (60% yield) of the title compound as a colorless non-viscous oil. 1H NMR (CDCl3) δ 1.01 (d, 6H, J=6.56 Hz), 2.05-2.08 (m, 1H), 3.67 (d, 2H, J=6.57 Hz), 6.77 (d, 2H, J=9.09 Hz), 7.36 (d, 2H, J=9.09 Hz).

後処理

  1. temperatureThe reaction is heated
  2. temperatureto reflux for four days
  3. extractionextracted with ether
  4. customthe organic layer is separated
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in hexane
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered through a plug of silica gel
  9. customThe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-11553213c5de40959df2fedb8bbf83ae
出典データセット
uspto-grants-2012_07
特許番号
US08222424B2

反応ノート

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