2-Bromonaphthalene → 2-(4-Nitrophenylthio)naphthalene

HRID 2395331ノート

反応式

HRID 2395331 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

参加物

6

反応物 3

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

生成物 1

HCID 189716852-(4-Nitrophenylthio)naphthalene収率 12%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 1049Pyridine溶媒

実験手順

2-Bromonaphthalene (0.08 moles, 16.6 g), 4-nitrothiophenol (0.08 moles, 12,4 g), potassium carbonate (0.1 moles, 13.4 g), copper bronze (6.0 g) and cuprous chloride (0.02 moles, 2.0 g) were heated under reflux for 4 days in 300 ml pyridine. The solution was filtered hot, concentrated, dissolved in ethyl acetate and washed thoroughly with 2N HCl and water. The solution was dried over sodium sulfate, concentrated and purified by HPLC over silica gel eluted with 5% ethyl acetate in hexane. The product was recrystallized from ethyl acetate and hexane to yield 2-(4-nitrophenylthio)naphthalene 2.6 g, 12% in the first crop. Mass spec. (FD) 281.

後処理

  1. filtrationThe solution was filtered hot
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed thoroughly with 2N HCl and water
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by HPLC over silica gel
  8. washeluted with 5% ethyl acetate in hexane
  9. customThe product was recrystallized from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-7fae9de9e87d408986b30100dba18b24
出典データセット
uspto-grants-1998_09
特許番号
US05814646

反応ノート

読み込み中…