Water → 2,4-Difluoro-5-iodobenzoic acid
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
Product 1
Reagents, catalysts & solvents 1
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
- additionAfter the completion of the addition
- stirringthe mixture was stirred for 1 hr
- filtrationThe precipitated solid was collected by filtration
- washwashed successively with water and hexane, and vacuum
- customdried
Sources & evidence
- ORD record
- ord-c162200d372c469987c198fc3343bb1f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635704B2
Reaction notes
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