甲苯 → 1-Nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene

HRID 32168

反应方程式

HRID 32168 反应方程式
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[CH2:5][C:4](OS(C(F)(F)F)(=O)=O)=[CH:3]1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)([O-:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(O)C>[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:4]1[CH2:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:17])([CH3:1])[CH:3]=1)([O-:20])=[O:19]

参与物

9

反应物 4

HCID 1140甲苯HCID 10340Carbonic acid sodium salt (1:2)HCID 27735482-硝基苯基硼酸HCID 59769424Trifluoromethanesulfonic acid 3,3,4,4-tetramethylcyclopent-1-enyl ester

产物 1

HCID 231417801-Nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene收率 99.8%

试剂、催化剂与溶剂 4

HCID 178418397HCID 178418397，化合物催化剂HCID 702乙醇溶剂HCID 8857乙酸乙酯溶剂HCID 57417360Sodium chloride; water溶剂

反应条件

温度
90 °C

实验过程

A mixture of the trifluoromethanesulfonic acid 3,3,4,4-tetramethylcyclopent-1-enyl ester (992 mg, 3.64 mmol) produced in Example (54a), 2-nitrophenylboronic acid (729 mg, 4.37 mmol), tetrakis(triphenylphosphine)palladium(0) (219 mg, 0.189 mmol), 2N aqueous solution of sodium carbonate (3.64 mL), toluene (12.5 mL) and ethanol (6.3 mL) was stirred for 6 hours at an external temperature of 90° C. under a nitrogen atmosphere. The reaction mixture was air-cooled to room temperature, and then ethyl acetate and brine were added and extraction was performed twice with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 891 mg of the title compound as a light brown oil.

后处理

  1. temperatureThe reaction mixture was air-cooled to room temperature
  2. extractionextraction
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

来源与证据

ORD记录
ord-9d1ee1ce6ed44d579d2fffaef459ebe4
来源数据集
uspto-grants-2008_09
专利号
US07425554B2

关联笔记

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