N-Iodosuccinimide → HCID 86666943, compound

HRID 511022Notes

Reaction equation

HRID 511022 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[CH:3]=1.[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[C:3]=1[I:13]

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 138501674'',5''-DICHLORO-2''-HYDROXYACETOPHENONE

Product 1

HCID 86666943HCID 86666943, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-(4,5-dichloro-2-hydroxyphenyl)ethanone (12 g, 59 mmol) in acetic acid (70 mL) was treated with N-iodosuccinimide (16 g, 71 mmol) and stirred at 90° C. for 18 hours. The reaction mixture was treated with additional N-iodosuccinimide (8 g, 36 mmol) and stirred at 90° C. for 4 hours. The reaction mixture was concentrated, diluted with EtOAc, and quenched with saturated sodium bicarbonate until the bubbling stopped. The organic layer was separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried and concentrated to give a brown solid. This material was recrystallized from methanol to give desired product (9.0 g, 46%) as a tan solid. LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9. Found: 330.8, 332.9.

Workup

  1. stirringstirred at 90° C. for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc
  4. customquenched with saturated sodium bicarbonate until the bubbling
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was re-extracted with EtOAc
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customto give a brown solid
  10. customThis material was recrystallized from methanol

Sources & evidence

ORD record
ord-6db47102e71c49408876507ce9169387
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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