1,4-Dioxane → HCID 86727067, compound
Reaction equation
Br[C:2]1[C:3]([F:12])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC.O1CCOCC1.C1C(=O)N([Br:44])C(=O)C1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C1COCC1.O>[Br:44][CH2:20][C:18]([C:2]1[C:3]([F:12])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8])=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
To a 500 mL flask was added 5-bromo-4-fluoro-2-methoxybenzonitrile (4.00 g, 17.4 mmol), Bis(Triphenylphosphine)Palladium(II)Chloride (0.61 g, 0.87 mmol), tributyl(1-ethoxy-vinyl)tin (9.42 mL, 26.1 mmol) followed by addition of 1,4 dioxane (40 mL). The resulting mixture was stirred at 95° C. for 3 h; the flask was taken out of the oil bath and cooled to rt followed by treatment with a mixture of THF/H2O (50/25 mL) and placed in an ice bath. To the flask was added NBS (6.19 g, 34.8 mmol) in small portions; after stirred for 0.5 h at 0° C., LC indicated formation of the desired product. The reaction mixture was taken out of the ice bath and slowly warmed up to rt. The reaction mixture was extracted with EtOAc (3×100 mL), washed with brine and water, it was then dried (Na2SO4), filtered and concentrated to dryness followed by separation over silica gel with the solvent systems of hexanes/EtOAc (1/0.5) to give the desired product. LC/MS: [(M+2)]+=274.
Workup
- temperaturecooled to rt
- customplaced in an ice bath
- stirringafter stirred for 0.5 h at 0° C.
Sources & evidence
- ORD record
- ord-752af153829348fdb8d6823ebb3255bc
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062070B2
Reaction notes
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