Diethyl Ether → 2-bromoethyl ethanesulfonate

HRID 436518Notes

Reaction equation

HRID 436518 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[CH2:5]([S:7](Cl)(=[O:9])=[O:8])[CH3:6].CCOCC>C(N(CC)CC)C>[CH2:5]([S:7]([O:4][CH2:3][CH2:2][Br:1])(=[O:9])=[O:8])[CH3:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 108982-BromoethanolHCID 11667Ethanesulfonyl chloride

Product 1

HCID 2463812-bromoethyl ethanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture containing 12.5 ml. of 2-bromoethanol, 12.9 ml. of ethane sulfonyl chloride and 100 ml. of ether was formed. Then, 14 ml. of triethylamine was added dropwise over a 55 minute period at 5°-10° C. and stirred for 1 hour. The mixture was allowed to come to room temperature and stirred for an additional 15 minutes. To the mixture was added 100 ml. of water, the ether layer was separated, dried over magnesium sulfate and evaporated to yield 17.6 grams of a yellow oil. nD30 1.4760.

Workup

  1. additionA mixture containing 12.5 ml
  2. customto come to room temperature
  3. stirringstirred for an additional 15 minutes
  4. additionTo the mixture was added 100 ml
  5. customof water, the ether layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-653874c9ea354ae29c1a5cdd6b874936
Source dataset
uspto-grants-1977_02
Patent number
US04009191

Reaction notes

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