Реакция #1531956

Уравнение реакции

ethyl acetate

3,5-Dinitrobenzyl chloride

2,3,3-trimethyl-3H-indol-5-yl-acetic acid

sodium bromide

→

solid

Выход 54.0%

1-(3,5-dinitrobenzyl)-5-(carboxymethyl)-3H-indolium Bromide

Выход 54.0%

Растворители

sulfolan

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   ДругоеThe crude reaction mixture
3. 3
   Фильтрацияthe dark brown solid was filtered OFF
4. 4
   workup.DISSOLUTIONdissolved in dimethylsulfoxide before purification by reverse phase chromatography

Методика

3,5-Dinitrobenzyl chloride (12.46 g, 57.5 mmol) was added to a solution of 2,3,3-trimethyl-3H-indol-5-yl-acetic acid (2.5 g, 11.5 mmol) with sodium bromide (5.92 g, 57.5 mmol) in sulfolan (10 ml). The reaction was heated at 100° C. for 20 hrs, then cooled to room temperature. The crude reaction mixture was added dropwise to an excess of ethyl acetate and the dark brown solid was filtered OFF and dissolved in dimethylsulfoxide before purification by reverse phase chromatography. The product was isolated as beige solid (54% yield). 1H NMR (d6-DMSO): δH: 8.75 (s, 1H), 8.45 (s, 2H), 7.15 (s, 1H), 6.95 (d, 1H), 6.70 (d, 2H), 5.10 (s, 2H), 3.95 (s, 2H), 3.45 (s, 3H), 1.40 (s, 6H). MALDI-TOF, m/z=398 (M+=398 for C20H20N3O6).

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