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Dimethylformamide → [1,1′-Biphenyl]-4-carboxylic acid, 2-(6,6-dimethyl-1-cyclohexen-1-yl)-2′-fluoro-5′-methoxy-, methyl ester

HRID 1662406
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HRID 1662406 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1I.CN(C=O)C.[CH3:26][C:27]1([CH3:42])[C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>[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>[CH3:26][C:27]1([CH3:42])[C:28]([C:11]2[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=2[C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:29][CH2:30][CH2:31][CH2:32]1
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 574676122-(6,6-Dimethyl-1-cyclohexen-1-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57705628Methyl 2'-fluoro-2-iodo-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706936[1,1′-Biphenyl]-4-carboxylic acid, 2-(6,6-dimethyl-1-cyclohexen-1-yl)-2′-fluoro-5′-methoxy-, methyl ester수율 48.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

To a stirred solution of 66.15D (0.750 g, 1.9 mmol) in DMF (4.00 mL, 52 mmol) at 23° C. was added 66.21B (0.92 g, 3.9 mmol), potassium carbonate (0.81 g, 5.8 mmol), and then tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The mixture was heated to 90° C. and stirred for 24 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 66.21C as a colorless oil (0.34 g, 48% 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-bd2a261bad154a12925ca2809be76ad7
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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