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Water → 4-(3-(Trifluoromethyl)pyridin-2-YL)benzoic acid

HRID 1391426
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HRID 1391426 반응식
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].O.[C:19](#N)[CH3:20]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([C:20]2[CH:19]=[CH:7][C:6]([C:12]([OH:13])=[O:15])=[CH:5][CH:4]=2)=[N:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 534262354-(3-(Trifluoromethyl)pyridin-2-YL)benzoic acid수율 81%

시약·촉매·용매 1

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매

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온도
160 °C

실험 절차

4-Bis(hydroxyl)boron-1-methylbenzoate (2.8 mmol) was dissolved in acetonitrile (2 ml) and added to a 5 ml microwave vessel. To the solution was 3.5 mmol of 2-chloro-3-trifluoromethylpyridine (633 mg), 34 mg of tetrakis(triphenylphosphine)-palladium(0). After stirring until dissolution, 8.4 mmol of potassium carbonate (1.16 g) was added, followed by 1 ml of water. The mixture was then heated at 160° C. for 300 seconds. After reaction completion, the solvents were evaporated under vacuum. The residue was dissolved in 2N KOH and THF and heated for 10 min. After hydrolysis, the THF was evaporated and the basic layer was washed with EtOAC. The aqueous layer was then acidified and extracted 3 times with EtOAc. The organic layers were combined and washed with water and brine. After drying, filtration and evaporation, the residue was prufied by HPLC to give of the target compound as a white solid (602 mg; 81%).

후처리

  1. additionadded to a 5 ml microwave vessel
  2. additionwas added
  3. customAfter reaction completion
  4. customthe solvents were evaporated under vacuum
  5. dissolutionThe residue was dissolved in 2N KOH
  6. temperatureTHF and heated for 10 min
  7. customAfter hydrolysis
  8. customthe THF was evaporated
  9. washthe basic layer was washed with EtOAC
  10. extractionextracted 3 times with EtOAc
  11. washwashed with water and brine
  12. customAfter drying
  13. filtrationfiltration and evaporation

출처 및 근거

ORD 기록
ord-bf01f8c01679416abdc35f0a9cbe5046
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07338950B2

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