Pyridine → beta-Bromo-beta-nitrostyrene

HRID 2253877Notes

Reaction equation

HRID 2253877 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8](Br)[CH:9]([Br:13])[N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.N1C=CC=CC=1>C1CCCCC1>[N+:10]([C:9]([Br:13])=[CH:8][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 1049PyridineHCID 15269112HCID 15269112, compound

Product 1

HCID 23555beta-Bromo-beta-nitrostyrene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

To a refluxing solution of 1-(4-chlorophenyl)-1,2-dibromo-2-nitroethane (from example 1) in cyclohexane (200 mL) is added a solution of pyridine (6 mL, 74 mmoles) in cyclohexane (200 mL) over a 1 hour period. The mixture is refluxed for an additional hour. The refluxing mixture is then extracted with approximately 200 mL of dilute HCL and 2×200 mL H2O. The organic layer is dried over magnesium sulfate (anhydrous) filtered, and the solvent removed from the filtrate by evaporation to yield a yellow solid. The solid is recrystallized from cyclohexane to give beta-nitrobromostyrene.

Workup

  1. temperatureThe mixture is refluxed for an additional hour
  2. extractionThe refluxing mixture is then extracted with approximately 200 mL of dilute HCL and 2×200 mL H2O
  3. dry with materialThe organic layer is dried over magnesium sulfate (anhydrous)
  4. filtrationfiltered
  5. customthe solvent removed from the filtrate by evaporation
  6. customto yield a yellow solid
  7. customThe solid is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-92eb4859e3cf452e8687917dfec831e4
Source dataset
uspto-grants-1993_08
Patent number
US05233052

Reaction notes

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