Hydrochloric Acid → 3-Fluoro-4-formylbenzoic acid

HRID 2233056Notes

Reaction equation

HRID 2233056 reaction equation
Br[CH:2](Br)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[F:12].Cl.[OH2:15]>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[F:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH:2]=[O:15])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 592951004-(Dibromomethyl)-3-fluorobenzoic acid

Product 1

HCID 212845583-Fluoro-4-formylbenzoic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

AgNO3 (0.39 mol) in hot H2O (90 mL) is added dropwise to a solution of crude 4-dibromomethyl-3-fluorobenzoic acid (2, 0.19 mol) in ethanol (EtOH) (480 mL) at 50° C. over 10 min and then the mixture is stirred at the same temperature for 45 min. After cooling to room temperature, the mixture is poured into 1 N HCl (200 mL) and filtered off. The residue is washed with EtOH and the filtrate is concentrated to ca. 300 mL. The mixture is extracted twice with ethylacetate (EtOAc) and the combined organic layers are washed with brine, dried over MgSO4 and evaporated in vacuo. The crystals are collected by filtration and washed with ether/hexane (1:1) to give 3-fluoro-4-formyl benzoic acid (3).

Workup

  1. filtrationfiltered off
  2. washThe residue is washed with EtOH
  3. concentrationthe filtrate is concentrated to ca. 300 mL
  4. extractionThe mixture is extracted twice with ethylacetate (EtOAc)
  5. washthe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. filtrationThe crystals are collected by filtration
  9. washwashed with ether/hexane (1:1)

Sources & evidence

ORD record
ord-692b60c9434f4ceea743837c05705718
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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