4-Bromophenol → 3-(4-Bromophenoxy)propan-1-ol

HRID 70569Notes

Reaction equation

HRID 70569 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][OH:11].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:8][CH2:9][CH2:10][OH:11])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 25517Ammonium Chloride

Product 1

HCID 187610183-(4-Bromophenoxy)propan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (12.0 g) and 3-bromo-1-propanol (5.1 mL) were added to a solution of 4-bromophenol (5.0 g) in N,N-dimethylformamide (200 mL) under ice-cooling, and the mixture was stirred at room temperature for 8.5 hours. The reaction solution was ice-cooled and a saturated ammonium chloride solution and water were added, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1→4:1→3:1) to give 3-(4-bromophenoxy)propan-1-ol as a crude product.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1→4:1→3:1)

Sources & evidence

ORD record
ord-0739e0d3327c47fbb592dc82457ebcaf
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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