Citric Acid → 1-(5-Trifluoromethoxy-1H-indol-3-yl)-ethanone
Reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[Cl-].C([Al+]CC)C.[C:21](Cl)(=[O:23])[CH3:22].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:21](=[O:23])[CH3:22]Participants
Procedure
To a solution of 5-(trifluoromethoxy)-1H-indole [262593-63-5] (1.00 g, 4.97 mmol) in CH2Cl2 (20 mL), cooled to 0° C., was added dropwise diethylaluminum chloride (1M solution in hexane; 7.46 mL, 7.46 mmol), and stirring was continued for 30 min. A solution of acetyl chloride (0.532 mL, 7.46 mmol) in CH2Cl2 (20 mL) was subsequently added, and the reaction mixture was stirred at 0° C. for 1 h. A 5% aqueous citric acid solution (100 mL) was then added at 0° C., and the mixture was stirred for 15 min at RT. The mixture (two phases) was filtered, and the precipitate was dried at 50° C. in vacuo for 1 h to afford the title compound. Beige solid. MS: 244.0 [M+H]+; tR (HPLC conditions c): 4.60 min. The material thus obtained was used directly in the next step without further purification
Workup
- stirringthe reaction mixture was stirred at 0° C. for 1 h
- stirringthe mixture was stirred for 15 min at RT
- filtrationThe mixture (two phases) was filtered
- customthe precipitate was dried at 50° C. in vacuo for 1 h
Sources & evidence
- ORD record
- ord-22fb0e3751504f9cb0b46d0af6e10691
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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