Methyl iodide → methyl 4-chloro-2-formylbenzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH:5]2[OH:12].I[CH3:14]>ClCCl>[CH3:14][O:6][C:7](=[O:11])[C:8]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[CH:5]=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-chloro-3-hydroxy-3H-isobenzofuran-1-one (10 g, 54 mmol) and iodomethane (80 g, 560 mmol) in dichloromethane (200 mL) was heated at reflux, then the heating bath was removed. To the above solution was added triethylamine (60 g) at a rate that maintained a brisk reflux. After the addition was completed, the mixture was allowed to cool to room temperature and stirred for 72 h. The mixture was purified by column chromatography to give the title product (1.5 g).
Workup
- temperatureat reflux
- customthe heating bath was removed
- additionTo the above solution was added triethylamine (60 g) at a rate
- temperaturethat maintained a brisk reflux
- additionAfter the addition
- customThe mixture was purified by column chromatography
Sources & evidence
- ORD record
- ord-e46004cb392f47538378463cd0c3cbb5
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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