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Potassium Carbonate → Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate

HRID 1662545
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HRID 1662545 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:7]1[C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 120175464-[[(Trifluoromethyl)sulfonyl]oxy]-1,3-benzenedicarboxylic acid dimethyl ester

생성물 1

HCID 57707138Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate수율 90.1%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매
HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

To a stirred solution of dimethyl 4-(trifluoromethylsulfonyloxy)isophthalate 66.13B (1.00 g, 2.9 mmol) in DMF (5.8 mL) at 23° C. was added 2,5-difluorophenylboronic acid (0.69 g, 4.4 mmol) (commercially available from Aldrich), and potassium carbonate (1.2 g, 8.8 mmol). Tetrakis(triphenylphosphine)palladium (0.24 g, 0.20 mmol) was then added to the mixture. The mixture was heated to 90° C. and was stirred for 17 hours. The reaction was then cooled to room temperature, diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 83.27A as a colorless oil (0.800 g, 89% yield).

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-696275f4ae994c9ea96b7db3a8e45ccb
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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