Acetonitrile → Ethyl 3-chloro-4-iodo-5-methoxybenzoate
Reaction equation
N[C:2]1[C:12]([O:13][CH3:14])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[Cl:15].C(#N)C.[I:19]CI.N(OCCC(C)C)=O>CCCCCCC.C(OCC)(=O)C>[Cl:15][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:13][CH3:14])[C:2]=1[I:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
To ethyl 4-amino-3-chloro-5-methoxybenzoate (15.8 g, 68.8 mmol) were added acetonitrile (40 mL) and diiodomethane (22.2 mL, 275 mmol) in that order, and then the mixture was stirred at 70° C. and isoamyl nitrite (13.9 mL, 103 mmol) was added dropwise over a period of 10 minutes. The mixture was then stirred at 70° C. for 40 minutes. After returning the mixture to room temperature, the solvent in the mixture was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 5/1) to obtain the title compound (15.6 g, 45.8 mmol).
Workup
- stirringThe mixture was then stirred at 70° C. for 40 minutes
- customto room temperature
- distillationthe solvent in the mixture was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography (
- additionmixture of n-heptane and ethyl acetate
Sources & evidence
- ORD record
- ord-cfae15e6fc0f46c9a0f38139eac18d33
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431603B2
Reaction notes
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