Thiophenol → 1-Nitro-3-(phenylsulfanyl)benzene

HRID 1428834

反応式

HRID 1428834 の反応式
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C=O)C>[C:1]1([S:7][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzene

生成物 1

HCID 1422321-Nitro-3-(phenylsulfanyl)benzene

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of thiophenol (1.0 g, 9.1 mmol), 3-iodonitrobenzene (1.9 g, 7.6 mmol), CuI (0.14 g, 0.76 mmol), K2CO3 (1.67 g, 12.1 mmol), and DMF (10 mL) was heated to 100° C. in a flame-dried sealed tube for 16 h. The mixture was allowed to cool and was poured over ice. The resulting mixture was extracted with EtOAc (2×), and the organic extracts were combined and washed sequentially with equal volumes of aqueous 1M HCl, water, and aqueous 1M NaOH. The solution was dried, concentrated, and the residue was purified by FCC (100:0 to 95:5 hexanes/EtOAc) to provide the titled compound, which was contaminated with ca. 10% thiophenol (1.43 g), and was taken on to subsequent steps without further purification.

後処理

  1. customsealed tube for 16 h
  2. temperatureto cool
  3. additionwas poured over ice
  4. extractionThe resulting mixture was extracted with EtOAc (2×)
  5. washwashed sequentially with equal volumes of aqueous 1M HCl, water, and aqueous 1M NaOH
  6. customThe solution was dried
  7. concentrationconcentrated
  8. customthe residue was purified by FCC (100:0 to 95:5 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-0bcc46a1b38348919cfa06ce86502a56
出典データセット
uspto-grants-2015_01
特許番号
US08937078B2

関連ノート

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