N-bromobutanimide → Methyl 5-bromo-1H-pyrrole-2-carboxylate
Reaction equation
COCCCC[N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13].[Br:16]N1C(=O)CCC1=O>ClCCl>[Br:16][C:11]1[NH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 1-(4-methoxybutyl)-1H-pyrrole-2-carboxylate (4.5 g) was dissolved in dichloromethane (30 ml), N-bromosuccinimide (4.0 g) was added and the mixture was stirred for 1 hr. The reaction mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:4) was concentrated under reduced pressure to give the object product (2.2 g).
Workup
- washThe reaction mixture was washed successively with water and brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- washa fraction eluted with ethyl acetate-hexane (1:4)
- concentrationwas concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-05aed2484370403183692ffd0c3f08b5
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045436B2
Reaction notes
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