N-bromobutanimide → HCID 19940138, compound

HRID 974351Notes

Reaction equation

HRID 974351 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:10]=1.[Br:16]N1C(=O)CCC1=O>O1CCCC1>[Br:16][C:9]1[CH:10]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[NH:7][C:8]=1[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 41751102,5-Di(thiophen-2-yl)-1H-pyrrole

Product 1

HCID 19940138HCID 19940138, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dithienylpyrrole (130 mg, 0.56 mmol) in 2.5 mL of anhydrous tetrahydrofuran cooled to -78° C. was added N-bromosuccinimide (99.68 mg, 0.56 mmol). After addition was complete the cooling bath was removed and the reaction mixture was allowed to stand in a -20° C. freezer for 4 hours, during which the solution became a brown color. The reaction mixture was concentrated under reduced pressure, carbon tetrachloride was added to precipitate the succinimide, and this mixture was filtered. The filter cake was washed with additional chloroform, the combined filtrates were concentrated, and the resulting oil was chromatographed on silica gel (50 g). Elution with hexane-ethyl acetate, 4:1, furnished 81 mg (46%) of 3-bromo-2,5-dithienylpyrrole.

Workup

  1. additionAfter addition
  2. customwas removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure, carbon tetrachloride
  4. additionwas added
  5. customto precipitate the succinimide
  6. filtrationthis mixture was filtered
  7. washThe filter cake was washed with additional chloroform
  8. concentrationthe combined filtrates were concentrated
  9. customthe resulting oil was chromatographed on silica gel (50 g)
  10. washElution with hexane-ethyl acetate, 4:1

Sources & evidence

ORD record
ord-c09e22c97d954a0889595db302d70d19
Source dataset
uspto-grants-1991_11
Patent number
US05068355

Reaction notes

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