Sulfuric Acid → 2-Fluoro-3-iodobenzoic acid

Reaction equation

[F:1][C:2]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6]C=1C#N.S(=O)(=O)(O)[OH:12].[O:16]1[CH2:21][CH2:20]OCC1>>[F:1][C:2]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:20]=1[C:21]([OH:16])=[O:12]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 312751,4-Dioxane

HCID 581542762-Fluoro-3-iodobenzonitrile

Product 1

HCID 110545892-Fluoro-3-iodobenzoic acidYield 82%

Conditions

Temperature: 115 °C

Procedure

A mixture of 2-fluoro-3-iodobenzonitrile (preparation 22a, 5.00 g, 20.2 mmol), dioxane (16 mL) and sulphuric acid (25 mL) was heated to 115° C. After 4 hours, the mixture was cooled and filtered. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give the title compound (4.42 g, 82%) as a solid.