1,6-Dibromohexane → 4-(6-Bromohexyloxy)-4'-nitrobiphenyl

HRID 2291258Notes

Reaction equation

HRID 2291258 reaction equation
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 123681,6-DibromohexaneHCID 2855718-Crown-6HCID 1380784-Hydroxy-4'-nitrobiphenylHCID 5462222Potassium

Product 1

HCID 200312344-(6-Bromohexyloxy)-4'-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 500 ml of toluene in a 100 ml round bottom flask, fitted with a condenser and magnetic stirrer, are added 7.6 g (0.03M) of the potassium salt of 4-hydroxy-4'-nitrobiphenyl, 36.6 g (0.15M) of 1,6-dibromohexane, and 0.5 g of 18-crown-6 ether. The mixture is refluxed for about 20 hours, and then filtered hot. The solvent is evaporated, and the residual crude product is recrystallized from hexane to provide purified product.

Workup

  1. temperatureThe mixture is refluxed for about 20 hours
  2. filtrationfiltered hot
  3. customThe solvent is evaporated
  4. customthe residual crude product is recrystallized from hexane
  5. customto provide
  6. custompurified product

Sources & evidence

ORD record
ord-f360704a57c143c7a3c6b8dd3e9919a2
Source dataset
uspto-grants-1989_01
Patent number
US04795664

Reaction notes

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