Hydrochloric Acid → Ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate

HRID 499992노트

반응식

HRID 499992 반응식
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:21]=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:23]=[C:24]([F:27])[C:25]=1F.Cl>CS(C)=O>[Cl:19][C:20]1[CH:21]=[C:22]([C:28]([F:29])([F:30])[F:31])[CH:23]=[C:24]([F:27])[C:25]=1[O:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2736496Benzene, 1-chloro-2,3-difluoro-5-(trifluoromethyl)-HCID 178473420Ethyl 5-methyl-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate

생성물 1

HCID 57548573Ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate수율 72.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
40 °C

실험 절차

To a DMSO (15 mL) solution of ethyl 3-hydroxy-5-methylpyrazole-1-carboxylate (1.36 g, 8.0 mmol) and potassium carbonate (1.1 g, 8.0 mmol) was added 3-chloro-4,5-difluorobenzotrifluoride (1.77 g, 8.0 mmol) and the mixture was stirred under heating at 40° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into 2 mol/L hydrochloric acid (30 mL) and extracted with ethyl acetate. The organic layers combined were washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The thus-obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7˜1:5) to give a white solid of ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate (2.14 g, yield: 72.9%). Melting point: 127˜129° C., 1H-NMR (CDCl3, TMS, ppm): δ1.40 (t, J=7.1 Hz, 3H), 2.53 (d, J=0.8 Hz, 3H), 4.41 (q, J=7.1 Hz, 2H), 5.81 (d, J=0.8 Hz, 1H), 7.38 (dd, J=2.1 Hz, JHF=9.5 Hz, 1H), 7.50˜7.60 (m, 1H).

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layers combined were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe thus-obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7˜1:5)

출처 및 근거

ORD 기록
ord-3c0fe6d0abc24a68b3166de2320de22f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767827B2

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