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

HRID 1428834

반응식

HRID 1428834 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 1422321-Nitro-3-(phenylsulfanyl)benzene

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0bcc46a1b38348919cfa06ce86502a56
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937078B2

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