Sulfuric Acid → 2-Fluoro-3-iodobenzoic acid

HRID 2096971Notes

Reaction equation

HRID 2096971 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

4

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 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.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. additionWater was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-aa40a567225948ffbedee37bd3881c95
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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