Water → ethyl 6-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 518125Notes

Reaction equation

HRID 518125 reaction equation
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:5][C:4]=2[CH:3]=1.[Br:15]N1C(=O)CCC1=O.O>O1CCCC1>[Br:15][C:7]1[C:8]2[S:9][C:2]([CH3:1])=[CH:3][C:4]=2[NH:5][C:6]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 1438928ethyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 1448019ethyl 6-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (1.0 g) in tetrahydrofuran (10 mL) was added N-Bromosuccinimide (0.94 g) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=97/3−76/24) to give the title compound (0.96 g).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=97/3−76/24)

Sources & evidence

ORD record
ord-d7dfb078f25547c38e55d5827a6a83b6
Source dataset
uspto-grants-2015_08
Patent number
US09115144B2

Reaction notes

Loading…