1-Bromopentane → 4-Bromo-4'-(pentyloxy)-1,1'-biphenyl

HRID 875246Notes

Reaction equation

HRID 875246 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.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenylYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under an argon atmosphere, 4-bromo-4′-hydroxybiphenyl (3.0 g, 12 mmol), 1-bromopentane (3.6 g, 24 mmol), and potassium carbonate (1.66 g, 12 mmol) were dissolved in acetone (60 mL) and stirred under a reflux condition for 24 hours. After they reacted with each other, liquid separation and extraction were performed with water and chloroform. After an organic layer was dried with anhydrous sodium sulfate and filtered, the solvent was distilled off under a reduced pressure. After the obtained reaction mixture was separated and purified with a silica gel column chromatography using chloroform as a moving bed, the mixture was purified by a recrystallization method using chloroform and hexane. Thereby, a white solid of 4-Bromo-4′-pentyloxybiphenyl (A1) was obtained (1.99 g, yield: 53%). The obtained product (A1) was identified by using a 1H-NMR method. 1H-NMR (CDCl3, 400 MHz) δ=7.53-7.51 (d, 2H), 7.48-7.46 (d, 2H), 7.42-7.40 (d, 2H), 7.00-6.95 (d, 2H), 4.01-3.98 (t, 2H), 1.81 (m, 2H), 1.42 (m, 4H), and 0.94 (t, 3H).

Workup

  1. customAfter they reacted with each other,
  2. customliquid separation and extraction
  3. dry with materialAfter an organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under a reduced pressure
  6. customAfter the obtained reaction mixture
  7. customwas separated
  8. custompurified with a silica gel column chromatography
  9. customthe mixture was purified by a recrystallization method

Sources & evidence

ORD record
ord-6f320b01a5d04479971267ff11fdb753
Source dataset
uspto-grants-2015_03
Patent number
US08981120B2

Reaction notes

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