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Isopropanol → 2'-Fluoro-4'-methylbiphenyl-2-carboxylic acid t-butyl ester

HRID 1517750
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HRID 1517750 반응식
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1Br)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(O)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>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.O.CCOC(C)=O>[C:1]([O:5][C:6]([C:7]1[C:8]([C:17]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=2[F:15])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:14])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 2783132(2-Fluoro-4-methylphenyl)boronic acidHCID 3804415tert-Butyl 2-bromobenzoate

생성물 1

HCID 592838992'-Fluoro-4'-methylbiphenyl-2-carboxylic acid t-butyl ester수율 96%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매2회
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

Compound A (22.8 g, 88.6 mmol) and 2-fluoro-4-methylphenylboronic acid (15.0 g, 97.4 mmol) were suspended in isopropyl alcohol (75 mL, 980 mmol). A solution of sodium carbonate (16 g, 150 mmol) in water (75 mL, 4.2 mol) was added and the mixture was degassed under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.0 g, 880 μmol) was then added and the mixture was stirred at 90° C. overnight. The mixture was cooled to room temperature, EtOAc (200 mL) and water (200 mL) were added, and the mixture was filtered. The liquor was extracted with EtOAc (2×100 mL), washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography (0-15% EtOAc in hexanes) to yield compound B as a colorless oil (14.9 g, 96% purity).

후처리

  1. customthe mixture was degassed under nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe mixture was filtered
  4. extractionThe liquor was extracted with EtOAc (2×100 mL)
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified by flash chromatography (0-15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-cd416af58d444b3090c3fe717adf75e5
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232306B2

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