Potassium Carbonate → 3-Chloro-5-(2,2,2-trifluoroethoxy)benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:27][C:28]([F:31])([F:30])[F:29])(=O)=O)=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:9]=1)[CH:5]=[O:6]Participants
5
Conditions
- Temperature
- 110 °C
Procedure
To a magnetically stirred solution of 3-chloro-5-hydroxybenzaldehyde (2.0 g, 12.8 mmol; see Example 1(ii) above) and potassium carbonate (2.3 g, 16.6 mmol) in DMF (35 mL) under nitrogen was added 2,2,2-trifluoroethyl p-toluenesulfonate (4.2 g, 16.6 mmol) at room temperature. The mixture was heated to 110° C. for 7 h and then stirred overnight at room temperature. The reaction was cooled to 0° C., poured into ice-cold 2 N HCl (100 mL) and extracted with EtOAc (2× 75 mL). The combined organic extracts were washed with 0.5 N HCl (2× 50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The brown oil was chromatographed on silica gel eluting with Hex:EtOAc (6:1) to afford the sub-title compound (1.9 g, 61%) as a yellow oil.
Workup
- temperatureThe reaction was cooled to 0° C.
- extractionextracted with EtOAc (2× 75 mL)
- washThe combined organic extracts were washed with 0.5 N HCl (2× 50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe brown oil was chromatographed on silica gel eluting with Hex
Sources & evidence
- ORD record
- ord-34102d87f4524e85b845b4ebd321f191
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645751B2
Reaction notes
Loading…