تفاعل #914

معادلة التفاعل

HCl

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

n-butyllithium

bromine

→

title compound

المردود 58.7%

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

المردود 58.7%

المذيبات

diethyl ether

—

hexanes

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر