Phosphorus oxychloride → Ethyl 4,6-dichloropicolinate

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[CH2:1]([O:3][C:4](=[O:13])[C:5]1[N+:6]([O-])=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:16])[N:6]=1)[CH3:2]

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 592585544-Chloropicolinic acid ethyl ester N-oxide

생성물 1

HCID 52982911Ethyl 4,6-dichloropicolinate수율 64%

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온도: 0 °C

실험 절차

4-Chloropicolinic acid ethyl ester N-oxide (1.6 g, 8 mmol) was added to 4 mL of phosphorus oxychloride at 0° C. and stirred at 0° C. for one hour. The solution was then heated at 100° C. for four hours. Excess POCl3 was removed in vacuo, and the residue was dissolved in ethyl acetate, washed with cold sodium bicarbonate solution, and extracted with ethyl acetate. Removal of the solvent gave 4,6-dichloropicolinic acid ethyl ester (compound A) as an off-white solid (1.12 g, 64%). The methyl ester can be made by an analogous procedure.

후처리

temperatureThe solution was then heated at 100° C. for four hours
customExcess POCl3 was removed in vacuo
dissolutionthe residue was dissolved in ethyl acetate
washwashed with cold sodium bicarbonate solution
extractionextracted with ethyl acetate
customRemoval of the solvent

출처 및 근거

ORD 기록: ord-5554f27f2e6c4dbab88e238591c802f7
출처 데이터셋: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07696202B2

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