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

HRID 1978712Notes

Reaction equation

HRID 1978712 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 219956731-Bromo-4-(2-hexyloxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (195 ml) was dissolved 2-(4-bromophenoxy)-1-ethanol (19. 5 g). To the mixture was added under ice-cooling 65% sodium hydride (5.3 g), and the mixture was stirred at room temperature for 2 hours. To the mixture was added dropwise iodohexane (19.9 ml), and the mixture was stirred for 2 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=8/1) to give 1-bromo-4-(2-hexyloxyethoxy)benzene (16.2 g).

Workup

  1. additionTo the mixture was added under ice-
  2. stirringthe mixture was stirred for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-8bdad6506ddb48bbbd6ed8c9beff3a63
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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