4-Bromobiphenyl → o-Quaterphenyl (8CI)

HRID 2397605Notes

Reaction equation

HRID 2397605 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>C1(C)C(C)=CC=CC=1>[C:2]1([C:15]2[C:14]([C:17]3[C:22]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=[CH:11][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 71014-BromobiphenylHCID 77304-Bromoanisole

Product 1

HCID 12549o-Quaterphenyl (8CI)

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The reaction is carried out as in Example 9 except that the 18.7 parts of 4-bromoanisole are replaced by 23.3 parts of 4-bromobiphenyl, and 110 parts of xylene are added as a solvent. After the reflux period, the reaction mixture is not steam distilled, but is cooled, and the solids present are collected by filtration, and washed on the filter with water and with 200 parts of toluene. The filter cake is dried, transferred to a Soxhlet extractor and continuously extracted for 96 hours with 100 parts of boiling dimethyl formamide. Quaterphenyl crystallises when the dimethyl formamide is cooled, and is collected and dried. 7.3 parts of quaterphenyl, m.p. 313°-317° are thereby obtained.

Workup

  1. additionare added as a solvent
  2. distillationdistilled
  3. temperatureis cooled
  4. filtrationthe solids present are collected by filtration
  5. washwashed on the
  6. filtrationfilter with water and with 200 parts of toluene
  7. customThe filter cake is dried
  8. extractioncontinuously extracted for 96 hours with 100 parts of boiling dimethyl formamide
  9. customQuaterphenyl crystallises when the dimethyl formamide
  10. temperatureis cooled
  11. customis collected
  12. customdried

Sources & evidence

ORD record
ord-528e1ec70856481ba8fb08cccca4b814
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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