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

HRID 32168

反応式

HRID 32168 の反応式
[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]

参加物

9

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 59769424Trifluoromethanesulfonic acid 3,3,4,4-tetramethylcyclopent-1-enyl ester

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9d1ee1ce6ed44d579d2fffaef459ebe4
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

関連ノート

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