4-Bromo-4'-methoxybiphenyl → 4-Metoxy-p-quaterphenyl

HRID 1085877Notes

Reaction equation

HRID 1085877 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[Ni].C1COCC1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 40340054-Bromo-4'-methoxybiphenyl

Product 1

HCID 200590574-Metoxy-p-quaterphenylYield 151.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

15 In another 1-liter three-necked flask, 31.5 g (120 mmol) of 4-bromo-4'-metoxybiphenyl and 108 mg (0.2 mmol) of NiC12(1,3-bis(diphenylphosphino)propane) (NiCl2 (dppp)) were added, which were dissolved into 500 ml of anhydrous THF. This solution was kept at 0° C. under a nitrogen atmosphere, and the Grignard reagent was added dropwise over a period of about 1 hour with stirring. During the addition, the orange color of the Ni catalyst disappeared, and the reaction mixture became brown. The reaction mixture was then refluxed with stirring for 5 hours to complete the reaction. After the reaction, the precipitated white solid was filtered, and washed with a small amount of THF. Recrystallization from sulforane gave 30.6 g (yield, 76%) of 4-metoxy-p-quaterphenyl (MQ). The liquid-crystal transition temperature of the MQ was 328° C.

Workup

  1. customwas kept at 0° C. under a nitrogen atmosphere
  2. additionDuring the addition
  3. temperatureThe reaction mixture was then refluxed
  4. stirringwith stirring for 5 hours
  5. customthe reaction
  6. customAfter the reaction
  7. filtrationthe precipitated white solid was filtered
  8. washwashed with a small amount of THF
  9. customRecrystallization from sulforane

Sources & evidence

ORD record
ord-0f460a1bcc864eb3ae9fd7def8e3fef0
Source dataset
uspto-grants-1991_04
Patent number
US05011879

Reaction notes

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