4-Iodophenol → 1-Fluoro-3-[(4-iodophenoxy)methyl]benzene

HRID 2184347Notes

Reaction equation

HRID 2184347 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13]Br.C([O-])C.[Na+]>C(O)C>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 680073-Fluorobenzyl bromideHCID 2723922Sodium ethoxide

Product 1

HCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.0 g (15.9 mmol) of 4-iodophenol and 3.49 g (15.9 mmol) of 3-fluorobenzyl bromide in 30 ml ethanol is treated dropwise at RT with 20 ml of a 1 molar solution of sodium ethanolate in ethanol. The reaction mixture is refluxed for 4 h and the precipitated sodium bromide is filtered off. The filtrate is evaporated to dryness, treated with 100 ml of water, acidified by addition of citric acid and extracted three times with dichloromethane. After drying and evaporation, the residue is subjected to chromatography on silica gel (hexane/ethyl acetate 9:1). This yields 4.23 g (81%) of a colorless solid. mp=48° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 h
  2. filtrationthe precipitated sodium bromide is filtered off
  3. customThe filtrate is evaporated to dryness
  4. additiontreated with 100 ml of water
  5. additionacidified by addition of citric acid
  6. extractionextracted three times with dichloromethane
  7. customAfter drying
  8. customevaporation

Sources & evidence

ORD record
ord-a74c3f780a8b4b3b84dae4163887afec
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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