Potassium Carbonate → 4-Bromo-4'-(heptyloxy)-1,1'-biphenyl

HRID 2297310Notes

Reaction equation

HRID 2297310 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 156472634-Bromo-4'-(heptyloxy)-1,1'-biphenylYield 88.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-bromo-4′-hydroxybiphenyl (5.05 g, 20.2 mmol) in DMF (100 ml) were added K2CO3 (4.20 g, 30.4 mmol) and 1 -bromoheptane (4.14 ml, 26.4 mmol), and then the mixture was heated at 80° C. After being stirred at 80° C. for 20 h, the mixture was cooled to room temperature. The mixture was diluted with Et2O (250 ml) and then the solution was washed with sat. brine (150 ml×2). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was recrystallized from CH2Cl2-petroleum ether to give 4-bromo-4′-heptyloxybiphenyl (6.21 g, 88%) as a white solid; FAB-MS: m/z 347[MH+].

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washthe solution was washed with sat. brine (150 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from CH2Cl2-petroleum ether

Sources & evidence

ORD record
ord-89a2d02fdbb040bc9e2525c5f626e8cb
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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