2-Furancarboxylic acid → 6-Fluoronaphthalene-1-carboxylic acid

HRID 329410Notes

Reaction equation

HRID 329410 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([OH:15])=[O:14]>[Cl-].[Al+3].[Cl-].[Cl-]>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=[CH:12]2

Participants

4

Reactant 2

HCID 69192-Furancarboxylic acidHCID 10008Fluorobenzene

Product 1

HCID 145813856-Fluoronaphthalene-1-carboxylic acidYield 6.1%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Conditions

Temperature
95 °C

Procedure

To a 1 liter round-bottomed flask equipped with condenser and N2 inlet were added 345 ml (3.68 mol) of fluorobenzene and 48 g (0.428 mol) of furoic acid. To the stirring suspension was added in portions 120 g (0.899 mmol of aluminum chloride. The reaction mixture was stirred at 95° C. for 16 hours and then quenched by addition to ice/water/1N HCl. After stirring 1 hour, the aqueous layer was decanted, and benzene and a saturated aqueous solution of sodium bicarbonate were added. After stirring 1 hour, the layers were separated, the aqueous layer washed with benzene, acidified, and extracted into ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over sodium sulfate, and evaporated to a solid. The solid was triturated with isopropyl ether to give 5.0 g (6.1%) of a white solid, NMR (DMSO-d6): 7.0-8.0 (m, 5H), 8.6 (m, 1H).

Workup

  1. customTo a 1 liter round-bottomed flask equipped with condenser and N2 inlet
  2. customquenched by addition to ice/water/1N HCl
  3. stirringAfter stirring 1 hour
  4. customthe aqueous layer was decanted
  5. additionbenzene and a saturated aqueous solution of sodium bicarbonate were added
  6. stirringAfter stirring 1 hour
  7. customthe layers were separated
  8. washthe aqueous layer washed with benzene
  9. extractionextracted into ethyl acetate
  10. washThe ethyl acetate layer was washed with water and brine
  11. dry with materialdried over sodium sulfate
  12. customevaporated to a solid
  13. customThe solid was triturated with isopropyl ether

Sources & evidence

ORD record
ord-69a0858a28ce4c0fbaa8b5ce6928cd75
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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