p-Fluoronitrobenzene → 2-(2-Nitro-5-fluorophenyl)-1-phenylethanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1([C:17]([O:19][Si](C)(C)C)=[CH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN([S+](N(C)C)N(C)C)C.C[Si-](F)(F)(C)C.BrBr.S(=O)(O)[O-].[Na+]>C1COCC1.C(#N)C.C1CCCCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH2:18][C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19])([O-:10])=[O:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2.12 mL (20 mmol) of 4-fluoronitrobenzene and 4.12 mL (21 mmol) of [(1-phenyl-1-ethenyl)oxy]trimethylsilane in 30 mL of THF at -78° C. was added 5.502 g (20 mmol) of TASF dissolved in 6 mL of acetonitrile and 5 mL of THF. After stirring for 3 hrs at -78° C., 1.00 mL (19.50 mmol) of bromine in 5 mL of cyclohexane was added dropwise. After being stirred for 15 min at -78° C., the mixture was warmed to room temperature and stirred further for 30 min. Thirty mL of saturated sodium bisulfite was added, and the product was extracted into four 60 mL portions of ether. The organic phase was washed with saturated sodium chloride, dried, and concentrated. Chromatography on silica using 30% ether/hexanes yielded the expected product. The yield was 1.660 g (38%) of product, which was an oil. The product material was analyzed by infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.
Workup
- stirringAfter being stirred for 15 min at -78° C.
- temperaturethe mixture was warmed to room temperature
- stirringstirred further for 30 min
- extractionthe product was extracted into four 60 mL portions of ether
- washThe organic phase was washed with saturated sodium chloride
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8afe861fd18a46178036afae127fb15d
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04912220
Reaction notes
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