Réaction #1531956

Équation de réaction

ethyl acetate

3,5-Dinitrobenzyl chloride

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

sodium bromide

→

solid

Rendement 54.0%

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

Rendement 54.0%

Solvants

sulfolan

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source