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

HRID 279477Notes

Reaction equation

HRID 279477 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 mixture of 2-bromobenzylalcohol (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, half-saturated aqueous sodium bicarbonate solution (300 ml) was added, and the mixture was extracted with dichloromethane (100 ml) twice. The extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1-bromo-2-(1-ethoxyethyl)oxymethylbenzene (25.44 g, yield: 98.2%) as a colorless oil.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (100 ml) twice
  4. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-788afae212e146e89ef312c7e97df4ca
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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