N-bromobutanimide → HCID 18470737, compound

HRID 2228626Notes

Reaction equation

HRID 2228626 reaction equation
[CH3:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH:6]=1.C1C(=O)N([Br:24])C(=O)C1>>[Br:24][C:6]1[NH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 13864178HCID 13864178, compound

Product 1

HCID 18470737HCID 18470737, compoundYield 96.7%

Procedure

To a solution of methyl 4-methyl-2-phenylpyrrole-3-carboxylate (74 mg, 0.341 mmol) in TEF (1.5 mL) was added NBS (67 mg, 0.375 mmol) at −78° C. After being stirred for 0.25 hour at the same temperature, the mixture was allowed to warm to room temperature. The mixture was poured into ice-water (5 mL). The whole was extracted with ethyl acetate (20 mL), dried over Na2SO4 and concentrated in vacuo. The residual oil was purified by flash chromatography eluting with ethyl acetate-hexane (1:8) to afford the subtitle compound (97 mg, 96% yield) as crystals.

Workup

  1. extractionThe whole was extracted with ethyl acetate (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residual oil was purified by flash chromatography
  5. washeluting with ethyl acetate-hexane (1:8)

Sources & evidence

ORD record
ord-075029089fda4ed48f8894421f067d83
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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