4-Bromophenol → p-Bromophenyl octyl ether

HRID 525975

Reaction equation

HRID 525975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 145298p-Bromophenyl octyl etherYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromophenol (10.46 g, 60.5 mmol), 1-bromooctane (15.43 g, 79.9 mmol) and potassiumcarbonate (90 g, 0.65 mol) in N,N-dimethylformamide and was heated to 90° C. for 4 h and then the potassiumcarbonate was filtered off. The reaction mixture was quenched with water and extracted three times with ether. The ether was then washed three times with 1M hydrochloric acid (HCl), one time with water, evaporated, and purified by distillation to obtain 1-bromo-4-(octyloxy)benzene (15.1 g, 52.9 mmol) as a colourless oil.

Workup

  1. filtrationthe potassiumcarbonate was filtered off
  2. customThe reaction mixture was quenched with water
  3. extractionextracted three times with ether
  4. washThe ether was then washed three times with 1M hydrochloric acid (HCl), one time with water
  5. customevaporated
  6. distillationpurified by distillation

Sources & evidence

ORD record
ord-cba53612026d4ccf92bb37ba1bbffbd2
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Linked notes

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