N-bromobutanimide → HCID 66914972, compound

HRID 880434Notes

Reaction equation

HRID 880434 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[NH:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:11]=1>O1CCOCC1.C(O)(=O)C>[Br:1][C:11]1[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:14][C:10]=1[CH3:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10868082HCID 10868082, compound

Product 1

HCID 66914972HCID 66914972, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromo succinimide (1.40 g, 7.87 mmol) was added to a solution of ethyl 5-methyl-3-phenyl-1H-pyrrole-2-carboxylate (1.5 g, 6.55 mmol) in a mixture of dioxane (10 mL) and acetic acid (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min. The reaction mixture was warmed to room temperature and stirred for another 15 min. The mixture was quenched with 2N NaOH solution and the organic layer was separated, washed with water, brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give ethyl 4-bromo-5-methyl-3-phenyl-1H-pyrrole-2-carboxylate (1.68 g, 84%) as a solid.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for another 15 min
  3. customThe mixture was quenched with 2N NaOH solution
  4. customthe organic layer was separated
  5. washwashed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-119fbd95faff484aaaf75339fbae9f7a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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