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

HRID 909997Notes

Reaction equation

HRID 909997 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.I[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CC(=O)CC>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
30 °C

Procedure

Anhydrous K2CO3 (416g, 3 mol) was added to a mixture of 4-bromo-4′-hydroxybiphenyl (300 g, 1.2 mol), 1-iodopentane (234 ml, 1.79 mol) and 2-butanone (600 ml). The reaction mixture was refluxed for 44 h until TLC (85:15 hexanes/EtOAc) showed complete consumption of the bromo alcohol. The mixture was cooled to about 30° C., diluted with CH2C12 (600 ml) and then filtered. The filtrate was washed twice with H2O and twice with a saturated aqueous NaCl solution, dried over anhydrous Na2SO4, filtered and then dried at reduced pressure to provide a solid. This solid was isolated by filtration, washed repeatedly with a total of 2 L of ice-cold heptane to remove all traces of iodopentane and then dried overnight under high vacuum. Yield: 340 g (88%) of a white powder.

Workup

  1. customconsumption of the bromo alcohol
  2. additiondiluted with CH2C12 (600 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed twice with H2O and twice with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customdried at reduced pressure
  8. customto provide a solid
  9. customThis solid was isolated by filtration
  10. washwashed repeatedly with a total of 2 L of ice-cold heptane
  11. customto remove all traces of iodopentane
  12. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-874cf70499a0427687df6ac02200c59a
Source dataset
uspto-grants-2011_09
Patent number
US08022033B2

Reaction notes

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