Methyl iodide → 2,4-Dichloro-6-methoxybenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[C:8]([Cl:10])[CH:9]=1)[CH:6]=[O:7].[C:12]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.CCOC(C)=O>[Cl:10][C:8]1[CH:9]=[C:2]([Cl:1])[CH:3]=[C:4]([O:11][CH3:12])[C:5]=1[CH:6]=[O:7]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4,6-dichlorosalicylaldehyde (2.69 mmol) in 5 mL DMF was added K2CO3 (5.39 mmol) followed by iodomethane (2.96 mmol). The reaction mixture was heated to 50° C. for 3.5 h. At RT, the mixture was diluted with EtOAc and washed 3 times with water and then with brine. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as beige solid.
Workup
- washwashed 3 times with water
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2dfbee47cdcf4435a633fa1b03fc2f42
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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