Diglyme → 4'-Fluoro(1,1'-biphenyl)-2-amine

HRID 1663240노트

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HRID 1663240 반응식
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].COCCOCCOC.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.B(O)O>C(O)C.C(OCC)(=O)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])=[CH:27][CH:26]=1

참가 물질

8

반응물 5

HCID 8150DiglymeHCID 10340Sodium CarbonateHCID 119922-Bromoaniline2회HCID 61668Boronic AcidHCID 2856454-Fluorophenylboronic acid

생성물 1

HCID 27589754'-Fluoro(1,1'-biphenyl)-2-amine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a stirred solution of 2-bromoaniline (1.72 g, 10.0 mmol) in diglyme (30 mL) tetrakis(triphenylphosphine)-palladium(0) (0.13 g, 0.3 mmol) and 2.0 M aqueous sodium carbonate solution (15 mL, 30.0 mmol) were added. In a separate flask, 4-fluorophenylboronic acid (2.23 g 16.0 mmol) was dissolved in ethanol (8 mL) and the mixture containing 2-bromoaniline was added to this boronic acid solution. The obtained brown reaction mixture was heated at 80° C. for 6 hours, then cooled, diluted with ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and n-hexane:ethyl-acetate=2:1 as eluent to yield after recrystallization from ethanol 1.8 g (60%) of the title compound as white crystals.

후처리

  1. temperaturecooled
  2. washwashed with saturated ammonium chloride solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. customethyl-acetate=2:1 as eluent to yield
  8. customafter recrystallization from ethanol 1.8 g (60%) of the title compound as white crystals

출처 및 근거

ORD 기록
ord-bde24fca292d47739a7e6cad5611ac38
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034827B2

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