4-Fluorophenylboronic acid → HCID 23499548, 화합물

HRID 1251881노트

반응식

HRID 1251881 반응식
C(=O)([O-])O.[Na+].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>COCCOC.[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>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)[CH:9]=1

참가 물질

6

반응물 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

생성물 1

HCID 23499548HCID 23499548, 화합물수율 138.3%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Saturated aqueous sodium hydrogen carbonate solution (50 ml) was added to a solution of methyl 4-methoxy-2-trifluoromethylsulfonyloxybenzoate (6.3 g; 0.02 mol) and 4-fluorobenzeneboronic acid (3.36 g; 0.024 mol) in DME (150 ml) at ambient temperature under an argon atmosphere. Tetrakis(triphenylphosphine) palladium (928 mg; 0.8 mmol) was then added and the reaction heated at reflux for 3.5 hours to give a homogeneous solution. After cooling to ambient temperature, the reaction was partitioned between ethyl acetate and water. The organic phase was washed with 2N HCl, water and brine, filtered through 1PS filter paper and the solvent removed in vacuo to give methyl 4-methoxy-2-(4-fluorophenyl)benzoate as a yellow oily solid (7.2 g) which was used without further purification.

후처리

  1. temperaturethe reaction heated
  2. temperatureat reflux for 3.5 hours
  3. customto give a homogeneous solution
  4. customthe reaction was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 2N HCl, water and brine
  6. filtrationfiltered through 1PS filter paper
  7. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-c938219961fe4e98a5943115c9105669
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342765B1

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