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

HRID 499992ノート

反応式

HRID 499992 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3c0fe6d0abc24a68b3166de2320de22f
出典データセット
uspto-grants-2010_08
特許番号
US07767827B2

反応ノート

読み込み中…