Acetonitrile → Ethyl 3-chloro-4-iodo-5-methoxybenzoate

HRID 41240Notes

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

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 this order, and the mixture was stirred at 70° C., and then isoamyl nitrite (13.9 mL, 103 mmol) was added dropwise thereto over 10 minutes. The mixture was stirred at 70° C. for 40 minutes. The mixture was returned to room temperature, the solvent was then distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (a mixed solvent 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 stirred at 70° C. for 40 minutes
customwas returned to room temperature
distillationthe solvent was then distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record: ord-02496be81bb3406ea0711670738f8315
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530504B2

Reaction notes

Loading…