Benzene → 4-Methoxy-3-fluoro-4"-cyano-p-terphenyl

HRID 36822Notes

Reaction equation

HRID 36822 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][C:31]=1[F:39]>C(O)C.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>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:32][C:31]=1[F:39]

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 13944624'-bromo-[1,1'-Biphenyl]-4-carbonitrileHCID 27821943-Fluoro-4-methoxyphenylboronic acid

Product 1

HCID 220796294-Methoxy-3-fluoro-4"-cyano-p-terphenylYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2.4 g of 4-bromo-4'-cyanobiphenyl, 0.37 g of tetrakis(triphenylphosphine)palladium(0), 15.2 ml of a 2N aqueous sodium carbonate solution, and 19.4 ml of benzene, a solution which was prepared by dissolving 1.9 g of 4-methoxy-3-fluoro-benzene boronic acid synthesized in [1] above in 14.4 ml of ethanol was slowly added dropwise with stirring, and the solution was subjected to reflux for 8 hours. After the reflux was finished, the solution was cooled, and the crystals thus precipitated were separated by filtration and washed with water and methanol in turn, and dried to obtain 2.5 g of 4-methoxy-3-fluoro-4"-cyano-p-terphenyl.

Workup

  1. customa solution which was prepared
  2. additionwas slowly added dropwise
  3. temperatureto reflux for 8 hours
  4. temperaturethe solution was cooled
  5. customthe crystals thus precipitated
  6. customwere separated by filtration
  7. washwashed with water and methanol in turn
  8. customdried

Sources & evidence

ORD record
ord-856c078c427a48308a9a01c4b78b789f
Source dataset
uspto-grants-1995_05
Patent number
US05417885

Reaction notes

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