Bromine → 2(4-Dibromomethylphenyl)pyridine

HRID 1066402ノート

反応式

HRID 1066402 の反応式
C1(C)C=CC(C2C=CC=CN=2)=CC=1.[Br:14]Br.[Br:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:19]=1>ClC1C=CC=CC=1>[Br:16][CH:17]([Br:14])[C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 24408BromineHCID 782192-(p-Tolyl)pyridineHCID 98875912-(4-Bromomethylphenyl)pyridine

生成物 1

HCID 98266562(4-Dibromomethylphenyl)pyridine収率 60.7%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
115 °C

実験手順

In a 100 ml four neck flask were placed 2-(4-tolyl)pyridine (5.0 g, 29.6 mmol) and chlorobenzene (18 ml), and bromine (9.4 g, 59.1 mmol) was added dropwise while heating the mixture at 110-120° C. over 12 hours. The reaction mixture was stirred with heating at a temperature in the above-mentioned range for 1 hour and analyzed by HPLC. As a result, 2-(4-bromomethylphenyl)pyridine was confirmed to have been produced in a 60.7% yield. The obtained reaction mixture was cooled and the precipitated 2-(4-bromomethylphenyl)pyridine salt was collected by filtration. The filtrate was neutralized with 5% aqueous sodium hydroxide solution. After washing with water, the mixture was dried over anhydrous magnesium sulfate. Chlorobenzene was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate-hexane) to give 2-(4-dibromomethylphenyl)pyridine in a 1.2 g yield. From the 1H-NMR analysis, the product was found to be 2-(4-dibromomethylphenyl)pyridine.

後処理

  1. additionwas added dropwise
  2. temperaturewith heating at a temperature in the above-mentioned range for 1 hour
  3. customto have been produced in a 60.7% yield
  4. customThe obtained reaction mixture
  5. temperaturewas cooled
  6. filtrationthe precipitated 2-(4-bromomethylphenyl)pyridine salt was collected by filtration
  7. washAfter washing with water
  8. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  9. customChlorobenzene was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-50dddf891cc949058a78d0eec2c3e6a2
出典データセット
uspto-grants-2001_06
特許番号
US06242608B1

反応ノート

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