N-Iodosuccinimide → HCID 86599455, compound

HRID 854905Notes

Reaction equation

HRID 854905 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=[O:5].[I:15]N1C(=O)CCC1=O>CN(C=O)C>[OH:1][C:2]1[C:9]([I:15])=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 86599455HCID 86599455, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (5.09 g, 24.7 mmole) and N-iodosuccinimide (13.9 g, 61.8 mmole) in anhydrous DMF (50 mL) was stirred at room temperature for 2 days under a dry N2 atmosphere. The solvent was removed in vacuo and the residue was dissolved in EtOAc (200 mL), washed with 0.5 N HCl (200 mL), H2O (200 mL), aqueous sodium thiosulfate (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid. Purification by sublimation under vacuum at 85° C. gave 7.97 g (97% yield) of the product as a white solid: EIHRMS m/z 331.9159 (M+, C8H8F3O4, Calc'd 331.9157).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washwashed with 0.5 N HCl (200 mL), H2O (200 mL), aqueous sodium thiosulfate (100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid
  8. customPurification by sublimation under vacuum at 85° C.

Sources & evidence

ORD record
ord-c02f8b4bdaf1463ba211f7ba9a5cefca
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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