Boron tribromide → 4-Hydroxy-p-quaterphenyl

HRID 1085878Notes

Reaction equation

HRID 1085878 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 200590574-Metoxy-p-quaterphenyl

Product 1

HCID 235086234-Hydroxy-p-quaterphenylYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

First, 25.2 g (75 mmol) of MQ obtained in section (L) mentioned above was suspended to 500 ml of methylene chloride in an 1-liter three-necked flask. To this suspension, 50 ml of a methylene chloride solution containing 19.0 g (75 mmol) of boron tribromide was added dropwise over a period of about 30 minutes with stirring under a nitrogen atmosphere. Then, the reaction mixture was refluxed for 10 hours with stirring under the nitrogen atmosphere. After the reaction was completed, the flask was cooled, and the solids that precipitated were obtained by filtration. The solids were washed with methylene chloride and dried. Then the solid was recrystallized with dimethylsulfoxide. In this way, 21.6 g (yield, 89%) of 4-hydroxy-p-quaterphenyl (HQ) was obtained as a white solid. The liquid-crystal transition temperature of HQ was 352° C.

Workup

  1. additionwas added dropwise over a period of about 30 minutes
  2. temperatureThen, the reaction mixture was refluxed for 10 hours
  3. stirringwith stirring under the nitrogen atmosphere
  4. temperaturethe flask was cooled
  5. customthe solids that precipitated
  6. customwere obtained by filtration
  7. washThe solids were washed with methylene chloride
  8. customdried
  9. customThen the solid was recrystallized with dimethylsulfoxide

Sources & evidence

ORD record
ord-31e32cb22afa4d63a7d58d82b89485a6
Source dataset
uspto-grants-1991_04
Patent number
US05011879

Reaction notes

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