Potassium Carbonate → 2-Chloro-4,5-difluorobenzaldehyde

HRID 253439Notes

Reaction equation

HRID 253439 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][OH:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 720763(2-Chloro-4,5-difluorophenyl)methanol

Product 1

HCID 152947152-Chloro-4,5-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-chloro-4,5-difluoro-phenyl)-methanol (120, 2.40 g, 0.0134 mol) in dichloromethane (40.0 mL) was added Dess-Martin periodinane (6.84 g, 0.0161 mol). The reaction was stirred at room temperature for 10 minutes. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (110, 1.7 g, 71.6%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 30% ethyl acetate in hexane
  7. customto give a white solid (110, 1.7 g, 71.6%)

Sources & evidence

ORD record
ord-18203bc781df4b6ab8587d6cd61ed527
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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