Реакция #535350

Уравнение реакции

Indomethacin

N-bromosuccinimide

→

(2-(Bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid

Растворители

tetrachloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was heated
2. 2
   Фильтрацияfiltered off from succinimide
3. 3
   ПромывкаThe solid was washed with hot tetrachloromethane (150 ml)
4. 4
   ДругоеThe solvent was evaporated in vacuo
5. 5
   workup.WAITPrepared 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetohypobromoanhydride was boiled in CCl4 (50 ml) for 1.5 h
6. 6
   Другоеused in further reactions without additional purification

Методика

Indomethacin A2 (R3=H, R1a=4-Cl) (1 g, 2.8 mmol) and N-bromosuccinimide (0.539 g, 3.08 mmol) were suspended in tetrachloromethane (50 ml) and kept at room temperature for 12 h. The reaction mixture was heated to boiling and filtered off from succinimide. The solid was washed with hot tetrachloromethane (150 ml). The solvent was evaporated in vacuo. Prepared 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetohypobromoanhydride was boiled in CCl4 (50 ml) for 1.5 h. 2-((2-(Bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid 1 h (R1=4-chlorobenzoyl, R3═R4═R5═H, R6═CH3) was prepared and used in further reactions without additional purification.

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