Isopropyl iodide → 1-Bromo-4-(propan-2-yloxy)benzene

HRID 1668714Notes

Reaction equation

HRID 1668714 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+].I[CH:16]([CH3:18])[CH3:17]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 2280881-Bromo-4-(propan-2-yloxy)benzeneYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromophenol (7.0 g, 40.0 mmol, 1 eq) dimethylsulfoxide (20 mL), and potassium carbonate (11.0 g, 80.0 mmol, 2.0 eq) was stirred at room temperature then 2-iodopropane (5.2 mL, 1.3 eq) was added. The mixture was heated to 60° C. overnight, cooled to room temperature and treated with water (200 mL). The reaction was extracted with dichloromethane, dried (sodium sulfate) and concentrated in vacuo. The crude was purified by flash chromatography eluting with cyclohexane to afford the title compound as a colorless oil (7.9 g, 92%);

Workup

  1. temperatureThe mixture was heated to 60° C. overnight
  2. temperaturecooled to room temperature
  3. extractionThe reaction was extracted with dichloromethane
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography
  7. washeluting with cyclohexane

Sources & evidence

ORD record
ord-42f2b3f60d0c4ab58f9e82e869a81630
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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