Water → 2,4-Difluoro-5-iodobenzoic acid

HRID 875061

Reaction equation

HRID 875061 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O.O>FC(F)(F)S(O)(=O)=O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 741022,4-Difluorobenzoic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 111297952,4-Difluoro-5-iodobenzoic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Conditions

Temperature
50 °C

Procedure

2,4-Difluorobenzoic acid (100 g, 633 mmol) was dissolved in trifluoromethanesulfonic acid (400 ml) and N-iodosuccinimide (157 g, 696 mmol) was added by portions at not more than 5° C. After the completion of the addition, the mixture was stirred at 50° C. for 1.5 hr. The reaction mixture was poured into iced water, and the mixture was stirred for 1 hr. The precipitated solid was collected by filtration, washed successively with water and hexane, and vacuum dried to give 2,4-difluoro-5-iodobenzoic acid (179 g yield quantitative) as a white solid.

Workup

  1. additionAfter the completion of the addition
  2. stirringthe mixture was stirred for 1 hr
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed successively with water and hexane, and vacuum
  5. customdried

Sources & evidence

ORD record
ord-7ba54a8e6b084dc0ba2d8f5b498bb7b7
Source dataset
uspto-grants-2015_03
Patent number
US08981103B2

Linked notes

Loading…