반응 #914

반응 방정식

HCl

N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

n-butyllithium

bromine

→

title compound

수율 58.7%

2-Bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

수율 58.7%

용매

diethyl ether

—

hexanes

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도to warm to room temperature
3. 3
   workup.STIRRINGstir for ca. 2 hours
4. 4
   workup.STIRRINGstirred at room temperature
5. 5
   온도The reaction mixture was cooled to 0° C.
6. 6
   기타The ether phase was separated
7. 7
   세척washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   농축concentrated in vacuo
10. 10
    기타The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes)

실험 절차

To a solution of 8.85 g (41 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 200 mL diethyl ether under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 36.0 mL (85 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ca. 15 minutes. To the reaction mixture was added 2.2 mL (41 mmol) of bromine dropwise. The light orange reaction mixture was allowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture darkened as it stirred at room temperature. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The ether phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes) affording 7.11 g of the title compound as an orange oil.

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