(1,1'-Biphenyl)-2-ol → HCID 66845232、化合物

HRID 1916420ノート

反応式

HRID 1916420 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 66845232HCID 66845232、化合物収率 388.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-03a09f6221314ae6a2225c77d8c7daca
出典データセット
uspto-grants-2013_12
特許番号
US08618097B2

反応ノート

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