反应 #914

反应方程式

HCl

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

n-butyllithium

bromine

→

title compound

收率 58.7%

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

收率 58.7%

溶剂

diethyl ether

—

hexanes

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGstir for ca. 2 hours
4. 4
   workup.STIRRINGstirred at room temperature
5. 5
   温度The reaction mixture was cooled to 0° C.
6. 6
   其他The ether phase was separated
7. 7
   洗涤washed with brine
8. 8
   干燥dried (MgSO4)
9. 9
   浓缩concentrated in vacuo
10. 10
    其他The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes)

实验过程

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.

来源