Methyl iodide → methyl 4-chloro-2-formylbenzoate

HRID 1728221Notes

Reaction equation

HRID 1728221 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

HCID 6328Methyl iodideHCID 12527053HCID 12527053, compound

Product 1

HCID 57566138methyl 4-chloro-2-formylbenzoateYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. temperatureat reflux
  2. customthe heating bath was removed
  3. additionTo the above solution was added triethylamine (60 g) at a rate
  4. temperaturethat maintained a brisk reflux
  5. additionAfter the addition
  6. 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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