1,6-Dibromohexane → HCID 23432392, compound

HRID 1783275Notes

Reaction equation

HRID 1783275 reaction equation
[OH:1][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.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>CC(C)=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 123681,6-DibromohexaneHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 23432392HCID 23432392, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.2 mol (39 g) of 4-hydroxy-4′-cyanobiphenyl, 2 mol (487.5 g) of 1,6-dibromohexane, 1.45 mol (200 g) of potassium carbonate anhydride and 800 ml of acetone were placed in a 2 l three-neck flask equipped with a mechanical stirrer and the mixture was reacted under reflux for 20 hours by using a water bath. The reaction mixture was cooled to ambient temperature and then undissolved salts were removed by filtration. The resulting reaction solution was concentrated to a volume of about ½ by using a rotary evaporator, to which was then added 500 ml of hexane, followed by heating with stirring. Then, the resulting solution was cooled gradually to ambient temperature and then allowed to stand in a freezing chamber to crystallize. After the crystallized product was subjected to vacuum filtration, it was washed with n-hexane and dried under reduced pressure to obtain a crude target product (yield: 85% (61.3 g)), which was then recrystallized from ethanol to obtain a purified target product 4-(6-bromohexyloxy)-4′-cyanobiphenyl (yield: 58% (41.8 g)).

Workup

  1. customequipped with a mechanical stirrer
  2. customthe mixture was reacted
  3. temperatureunder reflux for 20 hours
  4. customundissolved salts were removed by filtration
  5. customThe resulting reaction solution
  6. concentrationwas concentrated to a volume of about ½
  7. customa rotary evaporator
  8. additionto which was then added 500 ml of hexane
  9. temperatureby heating
  10. temperatureThen, the resulting solution was cooled gradually to ambient temperature
  11. customto crystallize
  12. filtrationAfter the crystallized product was subjected to vacuum filtration, it
  13. washwas washed with n-hexane
  14. customdried under reduced pressure
  15. customto obtain a crude target product (yield: 85% (61.3 g)), which
  16. customwas then recrystallized from ethanol

Sources & evidence

ORD record
ord-da7925d1e221449597eedc6d7ef7eec3
Source dataset
uspto-grants-2009_03
Patent number
US07501210B2

Reaction notes

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