Pyridine → HCID 86669331, compound

HRID 2178050Notes

Reaction equation

HRID 2178050 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:15])[C:11]=1[O:12]CC)[CH:7]=[O:8])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:15])[C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 86669349HCID 86669349, compound

Product 1

HCID 86669331HCID 86669331, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3,4-diethoxy-5-fluorobenzaldehyde (300 mg, 1.4 mmol) in DCM (50 mL) was added AlCl3 (207 mg, 1.55 mmol), and at 0° C., pyridine (230 mg, 2.8 mmol) was added, and the resulting mixture was refluxed overnight. The reaction mixture was cooled to room temperature, poured into ice water solution, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography on silica gel to give 3-ethoxy-5-fluoro-4-hydroxybenzaldehyde (160 mg).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-613f06c338cf479193e8c32e33902b35
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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