Water → 1-bromo-2-propoxybenzene

HRID 1978721Notes

Reaction equation

HRID 1978721 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH3:18].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 179525341-bromo-2-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (120 ml) was dissolved 2-bromophenol (12 g). To the mixture was added potassium carbonate (12.5 g) and then was added bromopropane (7.2 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 1-bromo-2-propoxybenzene (10.5 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customUnder reduced pressure, the solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-ded96d5b1a7c456db3da5e20a5cf4f09
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

Loading…