Bromine → 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone

HRID 2217181Notes

Reaction equation

HRID 2217181 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Br:12]Br>C(Cl)(Cl)Cl.O>[Br:12][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])[NH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

HCID 27981401-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanoneYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-trichloracetyl pyrrole (10.6 g, 50 mmoL) in CHCl3 (10 mL) was cooled to 0° C. and to this solution bromine (8.53 g, 53.5 mmoL) was added in a dropwise fashion. The reaction mixture was stirred for 10 minutes at 0° C. then 30 minutes at room temperature. The solution was diluted with H2O and extracted with CHCl3, washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 then concentrated in vacuo. The crude product was recrystallized from hexane and the product was obtained as white crystalline solid (8.0 g). HPLC Rt 5.66 min and MS 287.9 as M−1 peak.

Workup

  1. additionwas added in a dropwise fashion
  2. custom30 minutes
  3. customat room temperature
  4. extractionextracted with CHCl3
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationthen concentrated in vacuo
  8. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-8a104c7aa7c44553b812812fb778ec4b
Source dataset
uspto-grants-2008_08
Patent number
US07407962B2

Reaction notes

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