Benzene → 4-Methoxy-3'-fluoro-4"-cyanoterphenyl

HRID 1740674Notes

Reaction equation

HRID 1740674 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)=[C:16]([F:28])[CH:15]=1.C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:18]2[C:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=3)=[C:16]([F:28])[CH:15]=[CH:14][CH:19]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 120406114-Bromo-2-fluoro-4'-cyanobiphenylHCID 86645335(4-Methoxyphenyl)borate

Product 1

HCID 1317214144-Methoxy-3'-fluoro-4"-cyanoterphenylYield 47.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7.6 g of 4-methoxyphenyl borate dissolved in 60 ml of ethanol was dropped at room temperature into a mixture containing 13 g of 4-bromo-2-fluoro-4'-cyanobiphenyl, 0.5 g of tetrakis (triphenylphosphine) palladium, 90 ml benzene and 70 ml of a 2M potassium carbonate aqueous solution. This was then refluxed for five hours and cooled to room temperature, the reaction liquid was extracted with chloroform and washed three times with water, and the chloroform was removed. The residue that was obtained underwent vacuum distillation, and then was recrystallized from acetone to yield 6.6 g of 4-methoxy-3'-fluoro-4"-cyanoterphenyl. This compound exhibited a nematic liquid crystal phase, with a C-N point of 126° C. and an N-I point of 247.3° C.

Workup

  1. additionwas dropped at room temperature into a mixture
  2. temperatureThis was then refluxed for five hours
  3. customthe reaction liquid
  4. extractionwas extracted with chloroform
  5. washwashed three times with water
  6. customthe chloroform was removed
  7. customThe residue that was obtained underwent
  8. distillationvacuum distillation
  9. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-3f7d34c202ba4fe882c3f5883b1d56a5
Source dataset
uspto-grants-1999_10
Patent number
US05972240

Reaction notes

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