硝酸钾 → 2-硝基-5-(三氟甲氧基)苯甲酸

HRID 1717456

反应方程式

HRID 1717456 反应方程式
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O.CCOC(C)=O>[N+:15]([C:10]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8])([O-:17])=[O:16]

参与物

5

反应物 2

HCID 24434硝酸钾HCID 660963-(三氟甲氧基)苯甲酸

产物 1

HCID 219046132-硝基-5-(三氟甲氧基)苯甲酸

试剂、催化剂与溶剂 2

HCID 1118四氧化硫溶剂2 次HCID 8857乙酸乙酯溶剂

反应条件

温度
0 °C

实验过程

To a solution of 3-trifluoromethoxybenzoic acid (49.0 g, 0.24 mol) in sulfuric acid (500 mL) at less than 0° C. (ice-MeOH bath) was added a solution of potassium nitrate (31.3 g, 0.31 mol) in sulfuric acid (200 mL) over 20 minutes. The resulting solution was stirred at 0° C. for 2 hours, then warmed to room temperature and stirred for 18 hours. The reaction was poured into ice and the resulting acidic solution was extracted with EtOAc (5×). The combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc. The crude sub-title compound was dissolved in EtOAc and toluene and concentrated in vacuo to give a HOAc free solid (58.4 g, 97%) that was used in the next step without further purification.

后处理

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 hours
  3. additionThe reaction was poured into ice
  4. extractionthe resulting acidic solution was extracted with EtOAc (5×)
  5. washThe combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc
  10. concentrationtoluene and concentrated in vacuo
  11. customto give a HOAc free solid (58.4 g, 97%) that
  12. customwas used in the next step without further purification

来源与证据

ORD记录
ord-366a86e84b864851aafba423aef1dc68
来源数据集
uspto-grants-2010_09
专利号
US07803954B2

关联笔记

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