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

HRID 1810172Notes

Reaction equation

HRID 1810172 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 153241111-Bromo-4-(2-methylpropoxy)benzeneYield 60.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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) 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).

Workup

  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

Sources & evidence

ORD record
ord-1bbfacf3f50f42a686a514d8176349d2
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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