Water → tert-Butyl 3-bromo-1H-pyrrole-1-carboxylate
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:19][C:20]1[CH:24]=[CH:23][N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=1.[O:35](C(OC(C)(C)C)=O)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=O.O>C1COCC1.CN(C1C=CN=CC=1)C>[C:39]([O:38][C:36]([N:22]1[CH:23]=[CH:24][C:20]([Br:19])=[CH:21]1)=[O:35])([CH3:42])([CH3:41])[CH3:40]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of TBAF (1.0 M in THF, 3.6 mL) was added to a solution of 3-bromo-1-triisopropylsilanyl-1H-pyrrole (1.0 g, 3.308 mmol) in THF (10 mL) and the mixture was stirred at room temperature for 30 minutes. (BOC)2O (0.866 g, 3.965 mmol) and DMAP (40 mg, 0.3308 mmol) were added to the reaction and the resulting mixture was stirred for 2 additional hours. Water was added, and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and with brine; dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc) to give 0.197 g (24% yield) of 3-bromo-pyrrole-1-carboxylic acid tert-butyl ester as a clear oil.
Workup
- stirringthe resulting mixture was stirred for 2 additional hours
- extractionthe mixture was extracted with EtOAc
- washThe combined organic extracts were washed with water and with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified via flash chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-b7adad826d1346d2a0b9a67aa0043b68
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776910B2
Reaction notes
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