Sodium Iodide → 2,6-Dichloro-4-(2-methoxyethoxy)benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:20][CH2:21][O:22][C:23](C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:20][CH2:21][O:22][CH3:23])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]Participants
6
Conditions
- Temperature
- 100 °C
Procedure
2,6-Dichloro-4-hydroxybenzaldehyde (0.5 g, 2.62 mmol), 1-bromo-2-methoxyethone (0.3 mL), sodium iodide (0.4 g, 0.4 mmol) and potassium carbonate (0.9 g, 6.55 mmol) were added in DMF (5 mL) and heated at 100° C. for 1 h under stirring. When the reaction was done, the reaction mixture was diluted with EtOAc and extracted three times with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The resulting solid was purified by normal phase chromatography (hexanes:EtOAc 3:1) to afford 2,6-dichloro-4-(2-methoxyethoxy)benzaldehyde.
Workup
- extractionextracted three times with water
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuum
- customThe resulting solid was purified by normal phase chromatography (hexanes:EtOAc 3:1)
Sources & evidence
- ORD record
- ord-220ba3c4f38f45da8e4db0e817a58928
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575353B2
Reaction notes
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