Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole

HRID 376435

반응식

HRID 376435 반응식
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15]Br)=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[OH2:21]>CS(C)=O.[Cu-]=O>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15][OH:21])=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

참가 물질

5

반응물 2

HCID 962WaterHCID 222807951-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole

생성물 1

HCID 222807401-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-bromomethyl pyrazole(2.5 g, 7.18 mmol) in DMSO (40 mL) was added copper(I) oxide(2.16 g, 15.08 mmol) and water (12 mL). The reaction mixture was stirred at 60° C. for 2 hours then cooled to RT and stirred at RT overnight. The next day, the mixture was filtered through celite, filter pad was washed with ethyl acetate(20 mL); the filtrate was partitioned between ethyl acetate(50 mL) and water(50 mL); organic phase was separated and washed with water(3×30 mL); dried over sodium sulfate; filtered, concentrated, flash chromatography (ethyl acetate : hexane, 1:6) to afford 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole(1.7 g). CI mass spectrum m/z (rel. intensity) 286 (M+H, 100).

후처리

  1. temperaturethen cooled to RT
  2. stirringstirred at RT overnight
  3. filtrationThe next day, the mixture was filtered through celite
  4. filtrationfilter pad
  5. washwas washed with ethyl acetate(20 mL)
  6. customthe filtrate was partitioned between ethyl acetate(50 mL) and water(50 mL)
  7. customorganic phase was separated
  8. washwashed with water(3×30 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-db60bfc85dff428f94cba57dd6b8eb3a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020357

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