Iodine → 1-(But-3-en-1-yl)-4-nitrobenzene

HRID 2254989Notes

Reaction equation

HRID 2254989 reaction equation
[I-].[Na+].Br[CH:4]([CH2:16]Br)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C.O.CC(C)=O>[CH2:6]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH2:5][CH:4]=[CH2:16]

Participants

8

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 19739335HCID 19739335, compound

Product 1

HCID 189934361-(But-3-en-1-yl)-4-nitrobenzeneYield 89.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 52.1 g of sodium iodide, 300 ml of acetone and 28.6 g of 1-(3,4-dibromobutyl)-4-nitrobenzene was stirred under reflux for 3.5 hours. After cooling the brown suspension was freed from solvent in vacuo and the brown residue was taken up in diethyl ether and water. The separated iodine was reduced by adding solid sodium thiosulphate. The colourless ether solutions were washed with water, dried with sodium sulphate and concentrated in vacuo. The residue (14.9 g) was distilled in a high vacuum, whereby 13.4 g of 1-(3-butenyl)-4-nitrobenzene were obtained as an almost colourless liquid; b.p. 86°-89° C./0.2 Torr.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. temperatureAfter cooling the brown suspension
  3. washThe colourless ether solutions were washed with water
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated in vacuo
  6. distillationThe residue (14.9 g) was distilled in a high vacuum

Sources & evidence

ORD record
ord-bf0ed1c74f014ce7ac56fc36bb6398c7
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

Loading…