Potassium Carbonate → 3-Ethynyl-4-fluoroaniline
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[C:15]#[C:16][Si](C)(C)C>CO>[C:15]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:8]=1[F:7])[NH2:12])#[CH:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
16 mg of potassium carbonate are added to a solution of 360 mg of 4-fluoro-3-[(trimethylsilyl)ethynyl]aniline in 5 ml of methanol. After stirring over night under argon and at a temperature in the region of 20° C., the medium is concentrated to dryness under reduced pressure, then taken up in 8 ml of water and neutralized with a few drops of hydrochloric acid (1 N), and then extracted three times with diethyl ether. The combined organic phases are dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure. 225 mg of 3-ethynyl-4-fluoroaniline are obtained in the form of a brown oil, the characteristics of which are the following:
Workup
- concentrationthe medium is concentrated to dryness under reduced pressure
- extractionextracted three times with diethyl ether
- dry with materialThe combined organic phases are dried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-97bb2ecf950040fa91bc37642970b40b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993565B2
Reaction notes
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