Potassium Carbonate → 3-Chloro-5-(2-fluoroethoxy)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+].[F:17][CH2:18][CH2:19]CS([O-])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH2:19][CH2:18][F:17])[CH:9]=1)[CH:5]=[O:6]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 3-chloro-5-hydroxybenzaldehyde (8.2 g, 52.5 mmol; see Example 1(ii) above) and potassium carbonate (9.4 g, 68.2 mmol) in DMF (10 mL) under nitrogen was added a solution of (2-monofluoroethyl)methanesulfonate (9.7 g, 68.2 mmol; see step (i) above) in DMF (120 mL) dropwise at room temperature. The mixture was heated to 100° C. for 5 h and then stirred overnight at room temperature. The reaction was cooled to 0° C., poured into ice-cold 2N HCl and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The brown oil was chromatographed on silica gel eluting with Hex:EtOAc (4:1) to afford the sub-title compound (7.6 g, 71%) as a yellow oil.
Workup
- temperatureThe reaction was cooled to 0° C.
- extractionextracted with EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe brown oil was chromatographed on silica gel eluting with Hex
Sources & evidence
- ORD record
- ord-929b9b55d51f45d396cf84bd180a3030
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645751B2
Reaction notes
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