Water → 1-Bromo-4-iodo-2-(phenoxymethyl)benzene

HRID 1038350Notes

Reaction equation

HRID 1038350 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[CH2:16]Cl.[Na+].[I-].O>[OH-].[K+].CC(C)=O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[CH2:16][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 5238Sodium IodideHCID 593463281-Bromo-2-(chloromethyl)-4-iodobenzene

Product 1

HCID 593463231-Bromo-4-iodo-2-(phenoxymethyl)benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Phenol (13 g) dissolved in aqueous 4 M KOH solution (60 mL) is added to 4-bromo-3-chloromethyl-1-iodo-benzene (41.0 g) dissolved in acetone (50 mL). NaI (0.5 g) is added and the resulting mixture is stirred at 50° C. overnight. Then, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 19:1).

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-9036fc6a6da0426e91eb044c255eaa32
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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