1,2-Dibromoethane → 1-[(2-Bromoethyl)thio]-4-nitrobenzene

HRID 1864674Notes

Reaction equation

HRID 1864674 reaction equation
[Br:1][CH2:2][CH2:3]Br.C(=O)([O-])[O-].[K+].[K+].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12]>C(#N)C>[Br:1][CH2:2][CH2:3][S:20][C:17]1[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

Product 1

HCID 146450871-[(2-Bromoethyl)thio]-4-nitrobenzeneYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

6.94 ml of 1,2-dibromoethane was diluted with 100 ml of acetonitrile, mixed with 11.2 g of potassium carbonate and 5.0 g of 4-nitro-benzenethiol, and stirred at 80° C. for 18 hours. After washing with 300 ml of distilled water and with 300 ml of aqueous NaCl, the resulting organic layer was dried over magnesium sulfate, filtrated, and distilled under a reduced pressure. The residue obtained thus was subjected to column chromatography to obtain 6.9 g of the title compound (yield 82%).

Workup

  1. washAfter washing with 300 ml of distilled water and with 300 ml of aqueous NaCl
  2. dry with materialthe resulting organic layer was dried over magnesium sulfate
  3. filtrationfiltrated
  4. distillationdistilled under a reduced pressure
  5. customThe residue obtained thus

Sources & evidence

ORD record
ord-361b3d9600a448c2b4e75f9e651434b1
Source dataset
uspto-grants-2009_12
Patent number
US07625926B2

Reaction notes

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