N-Iodosuccinimide → 1-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone

HRID 510942Notes

Reaction equation

HRID 510942 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([F:12])=[C:4]([I:13])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

Product 1

HCID 866668571-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (23.8 g, 126 mmol) in acetic acid (100 mL) was treated with N-iodosuccinimide (34.1 g, 151 mmol) and stirred at 70° C. for 2 hours. The reaction mixture was concentrated, diluted with EtOAc and quenched with sat. NaHCO3 solution. The organic layer was separated, washed with water, dried over MgSO4 and concentrated under reduced pressure to give the desired product to be used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. customquenched with sat. NaHCO3 solution
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fcb8817adc1452aba252d85dc052234
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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