Dimethylformamide → 1-Bromo-4-(propan-2-yloxy)benzene

HRID 993368Notes

Reaction equation

HRID 993368 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+].Br[CH:16]([CH3:18])[CH3:17].CN(C)C=O>[I-].[Na+].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

7

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 2280881-Bromo-4-(propan-2-yloxy)benzeneYield 17,052%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromophenol (30.0 g, 173 mmol), potassium carbonate (26.3 g, 190 mol), sodium iodide (0.60 g, 4 mmol), 2-bromopropane (85.1 g, 0.692 mmol), and N,N-dimethylformamide (173 mL) was warmed at 60° C. for 17 hours. The solution was cooled to room temperature and water (300 mL) was added. The solution was extracted with diethyl ether. The extract was washed with aqueous sodium hydroxide, water, and aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated. The product was purified by vacuum distillation to give 4-bromo-isopropoxybenzene (25.3 g, 118 mmol) as a colorless liquid.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe solution was extracted with diethyl ether
  3. washThe extract was washed with aqueous sodium hydroxide, water, and aqueous sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe product was purified by vacuum distillation

Sources & evidence

ORD record
ord-a8897fa773c44a5ba68af81cc420be8c
Source dataset
uspto-grants-2002_10
Patent number
US06472536B1

Reaction notes

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