Bromine → 1-[(4-Bromo-1H-pyrrol-2-yl)methylidene]pyrrolidin-1-ium bromide

HRID 2071692Notes

Reaction equation

HRID 2071692 reaction equation
[Br-:1].[NH:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[N+:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.BrBr>C(Cl)(Cl)Cl>[Br-:1].[Br:1][C:5]1[CH:4]=[C:3]([CH:7]=[N+:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:2][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 214118841-[(1H-Pyrrol-2-yl)methylidene]pyrrolidin-1-ium bromide

Product 1

HCID 214118451-[(4-Bromo-1H-pyrrol-2-yl)methylidene]pyrrolidin-1-ium bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 91.0 g of 1-(pyrrol-2-ylmethylene)pyrrolidmium bromide (0.397 mole) in 1300 ml of absolute chloroform is added dropwise with stirring and ice-cooling 63.4 g of bromine (0.397mole). A solid precipitates during addition. After the reaction mixture has been stirred at room temperature for 64 hours, the solvent is evaporated in vacuo and the residue is recrystallized from 3:1 chloroform-acetonitrile to give as an off-white solid 1-(4-bromopyrrole-2-ylmethylene)pyrrolidinium bromide; m.p. 226°-228° C.

Workup

  1. customA solid precipitates during addition
  2. stirringAfter the reaction mixture has been stirred at room temperature for 64 hours
  3. customthe solvent is evaporated in vacuo
  4. customthe residue is recrystallized from 3:1 chloroform-acetonitrile

Sources & evidence

ORD record
ord-876e9b72815a4648a5b14a36ebc2f5b2
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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