Pyridine → 3-Fluoro-4,5-dihydroxybenzaldehyde

HRID 924953Notes

Reaction equation

HRID 924953 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11]C)[C:9]=1[OH:10])[CH:5]=[O:6].[Al+3].[Cl-].[Cl-].[Cl-].N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5936643-Fluoro-4,5-dihydroxybenzaldehydeYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-fluoro-4-hydroxy-5-methoxybenzaldehyde (800 mg, 4.7 mmol) in DCM (50 mL) was added AlCl3 (680 mg, 5.1 mmol) portionwise, and at 0° C., pyridine (950 mg, 9.4 mmol) was added, and the resulting mixture was refluxed overnight. The reaction mixture was quenched with HCl ice-water solution, and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give the 3-fluoro-4,5-dihydroxybenzaldehyde as a pale solid (600 mg, yield 81%), which was used directly in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customThe reaction mixture was quenched with HCl ice-water solution
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3853a0b4c6ac43a5bf279a41ddc670a6
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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