Cesium carbonate → 5-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 1935440Notes

Reaction equation

HRID 1935440 reaction equation
O([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])S(C(F)(F)F)(=O)=O.[Cl:15][C:16]1[CH:23]=[C:20]([CH:21]=[O:22])[C:19](O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:12][C:11]([F:14])([F:13])[CH2:10][O:9][C:19]1[CH:18]=[CH:17][C:16]([Cl:15])=[CH:23][C:20]=1[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 124815-Chloro-salicylaldehydeHCID 18700072HCID 18700072, compound

Product 1

HCID 47709505-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Using a small volume of DMF, the trifluorethoxy triflate thus prepared was added to a mixture of 5-chlorosalicylaldehyde (5 g, 32 mmol) and cesium carbonate (21 g, 64 mmol) in DMF (50 mL) at room temperature. After stirring at room temperature overnight the solids were filtered off and the filtrate concentrated under reduced pressure. The residue was diluted with ether and washed well with water. Drying (Na2SO4) and concentration yielded the title compound as an oil: 1H NMR (CDCl3) δ10.42 (s, 1H), 7.84 (dd, J=2.6 Hz, 1H), 7.54 (m, 1H), 6.93 (d, J=8.8 Hz, 1H), 4.48 (qd, J=1.5, 7.8 Hz, 2H).

Workup

  1. filtrationwere filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. additionThe residue was diluted with ether
  4. washwashed well with water
  5. customDrying
  6. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-9caf8d4c1f104edb999e2ac6f8d0b844
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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