Potassium Phosphate, Tribasic → 6-Fluoro-4-nitrobiphenyl-3-carbonitrile

HRID 17531Notes

Reaction equation

Br[C:2]1[C:3]([F:13])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:3]1[C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

Conditions

Temperature: 75 °C

Procedure

5-Bromo-4-fluoro-2-nitrobenzonitrile (I-240) (9.1 g, 37.14 mmol) was dissolved in tetrahydrofuran (270 ml), and at room temperature, phenylboronic acid (9.06 g, 74.28 mmol), tripotassium phosphate (15.77 g, 74.28 mmol) and tetrakis(triphenylphosphine)palladium (2.15 g, 1.86 mmol) were added. After stirred under nitrogen atmosphere at 75° C. for 48 hours, this was cooled to room temperature. The insoluble matter was separated by filtration, the filtrate was concentrated under reduced pressure. The residue was fractionated with chloroform and aqueous saturated ammonium chloride solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate.

Workup

temperaturethis was cooled to room temperature
customThe insoluble matter was separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record: ord-c16728b9ee0a48caa07a48e8b5a39f6b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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