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

HRID 1978761Notes

Reaction equation

HRID 1978761 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4](C)[CH:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH3:19].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:17][CH:18]([CH3:19])[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenol

Product 1

HCID 153241111-Bromo-4-(2-methylpropoxy)benzeneYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-2-methylphenol (14.2 g) in DMF (75 ml) was added potassium carbonate (14.7 g), and to the mixture was added dropwise bromopropane (9.33 g). The mixture was stirred at 70° C. for 3 hours and cooled, and to the mixture was added water. The mixture was extracted with hexane, and the organic layer was washed with 1N sodium hydroxide solution and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give colorless oil of 4-bromo-2-methyl-propoxybenzene (10.6 g).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with hexane
  3. washthe organic layer was washed with 1N sodium hydroxide solution and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-b421c23d463d47f8b8bdaff674c5d582
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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