Potassium Carbonate → 5-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 1728196Notes

Reaction equation

HRID 1728196 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[F:11][C:12]([F:16])([F:15])[CH2:13]I.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:13][C:12]([F:16])([F:15])[F:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 47709505-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehydeYield 838.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-hydroxy-benzaldehyde (3.1 g, 2 mmol), 1,1,1-trifluoro-2-iodo-ethane (2.4 mL, 24 mmol), K2CO3 (5.5 g, 40 mmol) and KI (0.1 g) were mixed in DMF (20 mL). Then the mixture was irradiated under microwave at 180° C. for 1 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give title compound as a yellow solid (Yield: 4 g).

Workup

  1. customThen the mixture was irradiated under microwave at 180° C. for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N NaOH
  6. customThen the organic layer was separated
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-07a8f31170b8417182be68635644ed4b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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