Cesium carbonate → 1-Iodo-3-methylsulfanyl-5-nitro-benzene

HRID 418063Notes

Reaction equation

HRID 418063 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:14][S:15](C)=O.C[Si](C)(C)SC.C(=O)([O-])[O-].[Cs+].[Cs+]>CCOCC>[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([S:15][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2352691-Iodo-3,5-dinitrobenzeneHCID 86634271DMSO trimethyl(methylthio)silane

Product 1

HCID 498437351-Iodo-3-methylsulfanyl-5-nitro-benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-iodo-3,5-dinitrobenzene (15 g, 51 mmole) in 150 mL of DMSO trimethyl(methylthio)silane (10 mL, 70.6 mmol) was added slowly. The resulting reaction mixture turned purple at this point. Cesium carbonate 99.9% (23.13 g, 71.4 mmol) was then added. After stirring at room temperature for 18 h, the reaction mixture was diluted with 150 mL of ether, washed with 400 mL of saturated sodium bicarbonate solution and 150 mL of brine. The combined organic phase were then dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1-iodo-3-methylsulfanyl-5-nitro-benzene as a yellow solid. The crude material was used in the next step without further purification. HR-EI(+) m/e calcd for C7H6NO2SI (M+) 294.9164, found 294.9164.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 400 mL of saturated sodium bicarbonate solution and 150 mL of brine
  3. dry with materialThe combined organic phase were then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14304a5fe88d4c6b831ed810a163ecb8
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

Loading…