Sodium Sulfite → 2,3-Difluoro-5-iodobenzoic acid

HRID 1517995Notes

Reaction equation

HRID 1517995 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+].[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 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 108913672,3-Difluoro-5-iodobenzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

2,3-Difluorobenzoic acid (5.0 g, 31.6 mmol) was dissolved in trifluoromethanesulfonic acid (25 ml), and N-iodosuccinimide (8.55 g, 38.0 mmol) was added by portions at 0° C. under an argon stream. The mixture was stirred at room temperature for 3 hrs., and the reaction solution was poured into sodium sulfite in ice water. The mixture was stirred and the precipitate was collected by filtration, washed with water and vacuum-dried to give an object product (7.5 g, yield 84%) as a pale-pink solid.

Workup

  1. stirringThe mixture was stirred
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customvacuum-dried

Sources & evidence

ORD record
ord-38b37374bca84c2f8f9f6223620b7f9c
Source dataset
uspto-grants-2012_07
Patent number
US08232401B2

Reaction notes

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