(2-Fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanol → 2-Fluoro-5-(2-fluoropyridin-3-yl)benzaldehyde

HRID 335948Notes

Reaction equation

HRID 335948 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH2:15][OH:16].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 67383551(2-Fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866584942-Fluoro-5-(2-fluoropyridin-3-yl)benzaldehydeYield 187.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanol (2.54 g) was dissolved in dichloromethane (200 mL). Silica gel (30 mL) was added followed by pyridinium chlorochromate (5.31 g, 24.63 mmol). It was stirred at RT and monitored by TLC. Once the oxidation was complete the mixture was filtered through a pad of silica gel (10 mL) and washed with ethyl acetate. Evaporation under reduced pressure gave the desired 2-fluoro-5-(2-fluoropyridin-3-yl)benzaldehyde (4.71 g, 21.49 mmol, 87% yield) as an off white solid. MS m/z=220.1 [M+H]+. Calculated for C12H7F2NO: 219.05.

Workup

  1. additionSilica gel (30 mL) was added
  2. filtrationwas filtered through a pad of silica gel (10 mL)
  3. washwashed with ethyl acetate
  4. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-9151dffb4b1d4ca7bd12ae9340916a2d
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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