Water → 1-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone

HRID 1499667Notes

Reaction equation

HRID 1499667 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[I:13]N1C(=O)CCC1=O.O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([I:13])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 5982295'-Chloro-2'-hydroxy-4'-methylacetophenone

Product 1

HCID 114723941-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-(5-chloro-2-hydroxy-4-methylphenyl)ethanone (from Oakwood, 50.0 g, 271 mmol) in acetic acid (300 mL) was added N-iodosuccinimide (73.1 g, 325 mmol) and the resulting mixture was stirred on a heating mantle between 60˜80° C. over 3.5 hours then cooled to room temperature and stirred overnight. Water (500 mL) was added to the mixture in portions, which caused a dark solid to form. After stirring for 10 minutes, the solids were filtered, washing with additional water. The light to dark brown solids were dried under vacuum for 4 hours then air dried over the weekend to give 81.3 g (97%) of the desired product. LCMS calculated for C9H9ClI2 (M+H)+: m/z=310.9; Found: 311.0. 1H NMR (300 MHz, CDCl3): δ 13.21 (s, 1H), 7.71 (s, 1H), 2.65 (s, 3H), 2.63 (s, 3H) ppm.

Workup

  1. stirringstirred overnight
  2. customto form
  3. stirringAfter stirring for 10 minutes
  4. filtrationthe solids were filtered
  5. washwashing with additional water
  6. customThe light to dark brown solids were dried under vacuum for 4 hours
  7. customair dried over the weekend

Sources & evidence

ORD record
ord-aeb346245a894854b83f85c2ff78525c
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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