Potassium Carbonate → 3-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

HRID 1527750ノート

反応式

HRID 1527750 の反応式
Cl[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[CH:17]=[C:18]([OH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]>C(#N)C>[F:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[O:25][CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 4239233-(Chloromethyl)-1-methyl-1H-pyrazoleHCID 5209483-Fluoro-4-nitrophenol

生成物 1

HCID 828819703-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

To a solution of 3-(chloromethyl)-1-methyl-1H-pyrazole (15.6 g, 0.12 mol) in acetonitrile (200 mL) was added K2CO3 (67 g, 0.48 mol) followed by 3-fluoro-4-nitrophenol (19 g, 0.12 mol). The mixture was stirred at 90° Celsius overnight. When the reaction was complete, it was cooled to RT and the solvent was concentrated to dryness. The resulting residue was dissolved in DCM (500 mL) and then washed with water (500 mL). The organic phase was separated, concentrated to dryness and purified by recrystallization from ethyl acetate (100 mL) to give the title compound. MS (ESI): mass calcd. for C11H10FN3O3, 251.07; m/z found, 252.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 8.05-7.99 (t, 1H), 7.33 (d, J=3, 1H), 6.86-6.84 (m, 1H), 6.81-6.78 (m, 1H), 6.29 (d, J=3, 1H), 5.11 (s, 2H), 3.88 (s, 3H).

後処理

  1. temperatureit was cooled to RT
  2. concentrationthe solvent was concentrated to dryness
  3. dissolutionThe resulting residue was dissolved in DCM (500 mL)
  4. washwashed with water (500 mL)
  5. customThe organic phase was separated
  6. concentrationconcentrated to dryness
  7. custompurified by recrystallization from ethyl acetate (100 mL)

出典と根拠

ORDレコード
ord-ecf5c09e630349c1813448c63c5f1347
出典データセット
uspto-grants-2015_07
特許番号
US09089569B2

反応ノート

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