Acetic Anhydride → N-Acetyl-5-bromoindolyl acetate
Reaction equation
C([CH2:4][NH:5][C:6]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:7]=1[C:8](O)=O)(O)=O.[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].C(O[C:25](=[O:27])[CH3:26])(=O)C>>[C:25]([N:5]1[C:6]2[C:7](=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=2)[C:8]([O:18][C:16](=[O:19])[CH3:17])=[CH:4]1)(=[O:27])[CH3:26]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
2-(N-carboxymethylamino)-5-bromobenzoic acid (0.84 g, 3.4 mmol) and anhydrous sodium acetate (0.6 g, 7.3 mmol) were dissolved in 8 ml acetic anhydride. After stirred for 5 hours at 60° C., the reaction mixture was cooled down to room temperature. Sodium acetate was filtered off. The filtrate was evaporated, and the residue was dissolved in 100 ml ethyl acetate. 100 ml water and 20 ml saturated sodium bicarbonate were added to the solution, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (50 ml×2). The combined organic phases were washed with saturated sodium bicarbonate (100 ml×2), dried and evaporated to obtain a white solid (1-acetyl-5-bromo-3-acetoxyindole) (1.3 g, 25.4%).
Workup
- temperaturethe reaction mixture was cooled down to room temperature
- filtrationSodium acetate was filtered off
- customThe filtrate was evaporated
- dissolutionthe residue was dissolved in 100 ml ethyl acetate
- addition100 ml water and 20 ml saturated sodium bicarbonate were added to the solution
- customthe organic phase was separated
- extractionThe aqueous phase was extracted with ethyl acetate (50 ml×2)
- washThe combined organic phases were washed with saturated sodium bicarbonate (100 ml×2)
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-b3a6d836af634e4dbf7d3d29e77a6099
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642765B2
Reaction notes
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