Water → 1,1'-Biphenyl, 4-bromo-4'-(dodecyloxy)-

HRID 2369634Notes

Reaction equation

HRID 2369634 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.I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C([O-])([O-])=O.[K+].[K+].O>CC(=O)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 202821-IodododecaneHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 64257941,1'-Biphenyl, 4-bromo-4'-(dodecyloxy)-Yield 95%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4′-bromobiphenyl-4-ol (8.41 g, 33.8 mmol), 1-iodododecane (10 g, 33.8 mmol) and K2CO3 (18.64 g, 135 mmol) in butanone (100 mL) was heated at reflux. After 16 h the mixture was poured into water (200 mL), extracted with DCM (3×100 mL), washed with NaOH (2 M, 100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was washed with hot MeOH to give the title compound (13.37 g, 95%) as a colourless powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. extractionextracted with DCM (3×100 mL)
  4. washwashed with NaOH (2 M, 100 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. washThe residue was washed with hot MeOH

Sources & evidence

ORD record
ord-7d72097b009d48b7ab188e76cafdf70e
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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