Tetrabutylammonium Fluoride → N-(5-ethynyl-2-fluorophenyl)-2,2,2-trifluoroacetamide
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[CH:9]=[CH:8][C:7]=1[F:18])=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:12]([C:10]1[CH:9]=[CH:8][C:7]([F:18])=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:19])[F:20])[CH:11]=1)#[CH:13]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2,2,2-trifluoro-N-{2-fluoro-5-[(trimethylsilyl)ethynyl]phenyl}acetamide (5.3 g, 17 mmol) in THF (400 mL) was cooled to 0° C., and a 1.0 M solution of TBAF in THF (17 mL, 17 mmol) was added dropwise. The resulting mixture was stirred for 10 min. at 0° C. The reaction was quenched with H2O (150 mL), concentrated under reduced pressure, and extracted with DCM. The combined organic layers were concentrated under reduced pressure, and the crude solid was used in the next reaction without further purification. ES-LC/MS m/z=230 [M−H]−.
Workup
- customThe reaction was quenched with H2O (150 mL)
- concentrationconcentrated under reduced pressure
- extractionextracted with DCM
- concentrationThe combined organic layers were concentrated under reduced pressure
- customthe crude solid was used in the next reaction without further purification
Sources & evidence
- ORD record
- ord-bc466bcd1f6e4e45be74502f78d10c2f
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812022B2
Reaction notes
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