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

HRID 1041930Notes

Reaction equation

HRID 1041930 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 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 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. customThe combined extracts are dried
  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-f031f06f57e3459a898266a92de9d4cc
Source dataset
uspto-grants-2013_10
Patent number
US08557782B2

Reaction notes

Loading…