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

HRID 1857808Notes

Reaction equation

HRID 1857808 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-a9337dfebeef4260a91769222d54f866
Source dataset
uspto-grants-2000_11
Patent number
US06147231

Reaction notes

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