Imidazole → 3-Fluoro-5-(1H-imidazol-1-yl)benzoic Acid

HRID 2216756노트

반응식

HRID 2216756 반응식
Br[C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([F:9])[CH:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[C:15]([O-])([O-:17])=[O:16].[K+].[K+].O>CN(C=O)C>[F:9][C:4]1[CH:5]=[C:6]([CH:7]=[C:2]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:3]=1)[C:15]([OH:17])=[O:16]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 1363131-Bromo-3,5-difluorobenzene

생성물 1

HCID 219424903-Fluoro-5-(1H-imidazol-1-yl)benzoic Acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-Bromo-3,5-difluorobenzene (1.00 g, 5.18 mmol) was dissolved in anhydrous DMF (10 mL). The solution was chilled in an ice bath. Imidazole (0.36 g, 5.18 mmol) and K2CO3 (0.72 g, 5.18 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours, and at 80° C. for 0.24 hours. The reaction mixture was poured into water (100 mL) and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated. The intermediate 3-Fluoro-5-Bromo-(1H-imidazol-1-yl)-benzene was used directly in the next step. Using the standard cyanation procedure, 3-Fluoro-5-cyano-(1H-imidazol-1-yl)-benzene was prepared as a colourless solid. The crude product was used directly in the next step. Using the standard saponification procedure, the title compound was prepared as a colourless solid. The crude product was used directly in the next step.

후처리

  1. temperatureThe solution was chilled in an ice bath
  2. waitat 80° C. for 0.24 hours
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customwas prepared as a colourless solid

출처 및 근거

ORD 기록
ord-f54e3176518b481f9d755469a97d596f
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112595B2

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