氢溴酸 → 3-溴-4-三氟甲基苯甲酸

HRID 887287

反应方程式

HRID 887287 反应方程式
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].NC(N)=O.[OH-].[Na+].[BrH:25]>O>[Br:25][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6]

参与物

7

反应物 5

HCID 260氢溴酸2 次HCID 1176聚脲HCID 14798二甲基对苯二胺二盐酸HCID 6426513-氨基-4-三氟甲基苯甲酸HCID 23668193亚硝酸钠

产物 1

HCID 223375703-溴-4-三氟甲基苯甲酸

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次

反应条件

温度
75 °C

实验过程

3-Amino-4-trifluoromethylbenzoic acid (8.20 g, 40.0 mmol), prepared according to Astrid Giencke and Helmut Lackner, Liebigs Ann. Chem., 569-579:6 (1990), in 48% HBr (20 mL) and H2O (67 mL) at 0° C. was treated with NaNO2 (2.99 g) in small portions over 15 minutes. After stirring for 30 minutes, the mixture was treated with urea (0.250 g) and then the mixture was added dropwise to a solution of CuBr (10.0 g) in 48% HBr (40 mL) and H2O (100 mL). The reaction mixture was heated at 75° C., stirred for 2 hours, cooled to room temperature, and stirred overnight. The mixture was treated with 20% NaOH until the pH>10. The resulting blue copper salts were removed by filtration through Celite. The mixture was acidified to pH 1 with HCl, extracted with CH2Cl2 (3×200 mL), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.

后处理

  1. stirringstirred for 2 hours
  2. temperaturecooled to room temperature
  3. stirringstirred overnight
  4. customThe resulting blue copper salts were removed by filtration through Celite
  5. extractionextracted with CH2Cl2 (3×200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

来源与证据

ORD记录
ord-3f7c81b28cc94f25a91d4bda91786269
来源数据集
uspto-grants-2012_08
专利号
US08247413B2

关联笔记

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