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

HRID 1428834

Reaction equation

HRID 1428834 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 1422321-Nitro-3-(phenylsulfanyl)benzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0bcc46a1b38348919cfa06ce86502a56
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Linked notes

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