Diglyme → 4-氟-联苯-2-胺

HRID 1663240笔记

反应方程式

HRID 1663240 反应方程式
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

参与物

8

反应物 5

HCID 8150DiglymeHCID 10340Carbonic acid sodium salt (1:2)HCID 11992邻溴苯胺2 次HCID 61668Boronic AcidHCID 2856454-氟苯硼酸

产物 1

HCID 27589754-氟-联苯-2-胺

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
80 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-bde24fca292d47739a7e6cad5611ac38
来源数据集
uspto-grants-2011_10
专利号
US08034827B2

反应笔记

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