4-Bromophenol → 4-Bromo-2-iodophenol

HRID 2390245Notes

Reaction equation

HRID 2390245 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[I:9]N1C(=O)CCC1=O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 120273N-Iodosuccinimide

Product 1

HCID 109245324-Bromo-2-iodophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-bromophenol (35.0 g, 145 mmol) in acetic acid (250 ml) was treated with N-iodosuccinimide (32.5 g, 145 mmol) at RT. The reaction mixture was stirred at RT for 18 h. The reaction mixture was filtered to remove the solid and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography (silica) eluting with 1% methanol in chloroform to afford the title compound as a brown liquid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the solid
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude material was purified by column chromatography (silica)
  5. washeluting with 1% methanol in chloroform

Sources & evidence

ORD record
ord-531cd2d599a3461e98b0b6132260111e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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