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Water → 3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoic acid

HRID 68784
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HRID 68784 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1F)[C:5]([O:7]CC)=[O:6].[NH:14]1[CH:18]=[N:17][CH:16]=[N:15]1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:5]([OH:7])=[O:6]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 2737171Ethyl 3,4-difluorobenzoate

생성물 1

HCID 286045763-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

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온도
150 °C

실험 절차

To a solution of ethyl 3,4-difluoro-benzoate (1.5 g) in N,N-dimethylformamide (15 mL) is added 1,2,4-triazole (1.1 g) and K2CO3 (2.3 g) and the mixture is heated at 150° C. in a microwave oven for 30 min. After cooling to room temperature, water and ethyl acetate are added and the organic layer is dried (MgSO4) and concentrated. The residue is purified by chromatography on silica gel (ethyl acetate/hexane 0:1→1:0). The ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH (3 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is neutralized with 6 M aqueous HCl, concentrated and then acidified with 6 M aqueous HCl. The precipitate is filtered off washing with a small amount of water and dried by suction to give the title compound.

후처리

  1. temperatureAfter cooling to room temperature
  2. dry with materialthe organic layer is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography on silica gel (ethyl acetate/hexane 0:1→1:0)
  5. dissolutionThe ester is dissolved in methanol (30 mL)
  6. addition4 M aqueous NaOH (3 mL) is added
  7. concentrationconcentrated
  8. filtrationThe precipitate is filtered off
  9. washwashing with a small amount of water
  10. customdried by suction

출처 및 근거

ORD 기록
ord-f0c13f9742604d9499bb2c72aceabf04
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822471B2

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