4-Bromophenol → p-Bromophenyl octyl ether

HRID 1897374Notes

Reaction equation

HRID 1897374 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 The reaction mixture
  2. customwas 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-9ba2a5d6769e408dbb2b55d9a9fdaa1e
Source dataset
uspto-grants-2013_08
Patent number
US08519037B2

Reaction notes

Loading…