4-Chloro-2-fluoro-1-nitrobenzene → 4-Ethenyl-2-fluoro-1-nitrobenzene
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[CH:3]=1.[CH2:12]([Sn](CCCC)(CCCC)C=C)[CH2:13]CC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl-].[Li+]>C(Cl)(Cl)Cl.CO.CN1CCCC1=O>[CH:12]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[CH:3]=1)=[CH2:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
4-Chloro-2-fluoronitrobenzene (300 mg, 1.71 mmol), Pb2(dba)3 (236 mg, 0.228 mmol), tributyl (vinyl) tin (333 mg, 1.14 mmol), tri-2-furylphosphine (212 mg, 0.912 mmol) and lithium chloride (193 mg, 4.56 mmol) were added to methylpyrrolidinone (5 ml), and the mixture was stirred in a sealed tube at 120° C. for one hour. The mixture was diluted with chloroform-methanol, and filtered through a Celite Pad. After concentrating the filtrate, the concentrate was dissolved in ethyl acetate and washed with aqueous potassium fluoride. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and purified by thin-layer silica gel chromatography (hexane-ethyl acetate, 5:1) to give the title compound (146 mg) as a pale yellow oil.
Workup
- filtrationfiltered through a Celite Pad
- concentrationAfter concentrating the filtrate
- dissolutionthe concentrate was dissolved in ethyl acetate
- washwashed with aqueous potassium fluoride
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- custompurified by thin-layer silica gel chromatography (hexane-ethyl acetate, 5:1)
Sources & evidence
- ORD record
- ord-63e39d1133d5495d82c2cfdcd7b58636
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148224B2
Reaction notes
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