(1,1'-Biphenyl)-2-ol → HCID 66845232, 화합물

HRID 1480581노트

반응식

HRID 1480581 반응식
[C:1]1(C2C=CC=CC=2O)C=CC=C[CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([O-:24])=[O:23].[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[C:33](I)=[CH:32][C:31]=1[F:38].O1CCCC1>[NH4+].[Cl-].CCOC(C)=O.[Cu]I>[Cl:29][C:30]1[C:31]([F:38])=[CH:32][C:33]([CH:21]([C:22]([O:24][CH2:1][CH3:2])=[O:23])[C:20]([O:26][CH2:27][CH3:28])=[O:25])=[C:34]([F:36])[CH:35]=1

참가 물질

9

반응물 5

HCID 7017(1,1'-Biphenyl)-2-olHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 3595298Propanedioic acid, monoethyl esterHCID 510000881-Chloro-2,5-difluoro-4-iodobenzene

생성물 1

HCID 66845232HCID 66845232, 화합물수율 388.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
90 °C

실험 절차

Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by 1-chloro-2,5-difluoro-4-iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90° C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J=6.3, 9.3, 1H), 7.17 (dd, J=6.1, 8.9, 1H), 4.91 (s, 1H), 4.33-4.14 (m, 4H), 1.28 (t, J=7.2, 6H).

후처리

  1. customThe reaction mixture was sealed
  2. temperatureto cool to room temperature
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered through Celite
  6. customThe brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-03aad915c45c49e49c526ef2c309e37e
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409886B2

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