N-Iodosuccinimide → 2,3-Difluoro-5-iodobenzoic acid

HRID 1838120Notes

Reaction equation

HRID 1838120 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>FC(F)(F)S(O)(=O)=O>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 3705902,3-Difluorobenzoic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 108913672,3-Difluoro-5-iodobenzoic acidYield 79.6%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a cold (0° C.), stirred solution of 4.74 g of 2,3-difluorobenzoic acid in 15.0 mL of trifluoromethanesulfonic acid is added in portions 8.1 g of powdered N-iodosuccinimide. Following the addition, the mixture is allowed to warm to room temperature, stirred for 5 h, then poured onto 200 mL of cracked ice containing 5 g of sodium bisulfite. The mixture is stirred well for 15 m, then filtered, and the solid washed well with water and dried under vacuum to provide 6.78 g of the title compound as a solid.

Workup

  1. additionthe addition
  2. stirringThe mixture is stirred well for 15 m
  3. filtrationfiltered
  4. washthe solid washed well with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1282becd71904c4aa0e40f8483d16e57
Source dataset
uspto-grants-2004_01
Patent number
US06673793B2

Reaction notes

Loading…