Bromine → HCID 18967215, compound

HRID 2226265Notes

Reaction equation

HRID 2226265 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([O:15][CH3:16])[C:13]([C:17]#[N:18])=[C:12]([C:19]#[N:20])[CH:11]=2)=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:1][C:11]1[C:12]([C:19]#[N:20])=[C:13]([C:17]#[N:18])[N:14]([O:15][CH3:16])[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 15766628HCID 15766628, compound

Product 1

HCID 18967215HCID 18967215, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Bromine (0.341 g, 0.00213 mol) is added to a stirred mixture of 5-(p-chlorophenyl)-1-methoxypyrrole-2,3-dicarbonitrile (0.5 g, 0.00193 mol) and sodium acetate (0.318 g, 0.00388 mol) in acetic acid. The reaction mixture is heated at 95°-100° C. overnight, cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined ethyl acetate extracts are washed sequentially with water, saturated sodium bicarbonate solution, aqueous sodium metabisulfite solution, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a solid that is crystallized from ethyl acetate/hexanes to give the title compound as a yellow solid (0.406 g, 62%), mp 166.5°-167° C.

Workup

  1. temperatureThe reaction mixture is heated at 95°-100° C. overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate extracts are washed sequentially with water, saturated sodium bicarbonate solution, aqueous sodium metabisulfite solution, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a solid
  7. customthat is crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2aa7c288fa684fcd8b51e01117233a72
Source dataset
uspto-grants-1994_09
Patent number
US05347016

Reaction notes

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