4-Bromophenol → 1-bromo-4-(1-ethoxyethoxy)benzene

HRID 129361Notes

Reaction equation

HRID 129361 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[CH:9]([O:11][CH2:12][CH3:13])=[CH2:10].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:9]([O:11][CH2:12][CH3:13])[CH3:10])=[CH:1][CH:2]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 8023Ethyl vinyl etherHCID 516892Sodium Bicarbonate

Product 1

HCID 27237611-bromo-4-(1-ethoxyethoxy)benzeneYield 100%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

p-Bromophenol (50 g, 0.29 mole), ethyl vinyl ether (41.7 g, 0.58 mole) and pyridinium p-toluenesulfonate (1.5 g) were dissolved in methylene chloride (300 ml), followed by reaction with stirring at room temperature for 6 hours. Then 5% aqueous sodium bicarbonate (400 ml) was added to the reaction mixture, and stirred. Then, the organic layer was separated, washed with H2O (300 ml×3), dried over anhydrous MgSO4 and evaporated. The residue (82 g) was distilled under reduced pressure to give 71.1 g of p-bromo-(1-ethoxyethoxy)benzene as a pale yellow oil having a boiling point of 112°-114° C./6 mmHg.

Workup

  1. customfollowed by reaction
  2. stirringstirred
  3. customThen, the organic layer was separated
  4. washwashed with H2O (300 ml×3)
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. distillationThe residue (82 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-a8c05469dbbe4c58a020ca1a81482b36
Source dataset
uspto-grants-1995_11
Patent number
US05468589

Reaction notes

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