Ethyl vinyl ether → 1-Bromo-2-(1-ethoxyethyl)oxymethyl-benzene

HRID 342172Notes

Reaction equation

HRID 342172 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11].C(=O)(O)[O-].[Na+]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][CH:10]([O:12][CH2:13][CH3:14])[CH3:11]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 728502-Bromobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 154837851-Bromo-2-(1-ethoxyethyl)oxymethyl-benzeneYield 98.2%

Reagents, catalysts & solvents 2

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

Procedure

Pyridinium p-toluenesulfonate (0.50 g, 0.002 mol) was added to a mixed solution of 2-bromobenzyl alcohol (18.70 g, 0.1 mol), dichloromethane (150 ml) and ethyl vinyl ether (14.42 g, 0.2 mol) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a half-saturated aqueous solution (300 ml) of sodium bicarbonate was added, and the mixture was extracted with dichloromethane (100 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1-bromo-2-(1-ethoxyethyl)oxymethyl-benzene (25.44 g, Yield: 98.2%) as a colorless oil.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with dichloromethane (100 ml) twice
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98228457ea924d81a5c79bf97a4f9694
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

Loading…