苯胺 → Methyl 3-(phenylamino)benzoate

HRID 2422267

反应方程式

HRID 2422267 反应方程式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[NH:12]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参与物

6

反应物 4

HCID 6115苯胺HCID 10796碳酸氢铯HCID 120703-溴苯甲酸甲酯HCID 6348761,1'-联萘-2,2'-双二苯膦 (BINAP)

产物 1

HCID 614856Methyl 3-(phenylamino)benzoate收率 34.3%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

反应条件

温度
80 °C

实验过程

A mixture of methyl 3-bromobenzoate (5.87 g, 27.3 mmol), aniline (3.73 mL, 41.0 mmol), cesium carbonate (12.5 g, 38.2 mmol), tris(dibenzylidenacetone)dipalladium (0) (1.0 g, 1.09 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.02 g, 1.64 mmol) and toluene (60 mL) was stirred under a nitrogen atmosphere at 80° C. for 16 hrs. The reaction mixture was cooled, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (2.13 g, yield 34%) as pale-yellow crystalsitle compound.

后处理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

来源与证据

ORD记录
ord-322484b5bc5e4d83a72afe64281b1bcf
来源数据集
uspto-grants-2011_06
专利号
US07960369B2

关联笔记

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