Diethyl Ether → 2-bromoethyl ethanesulfonate

HRID 1579129Notes

Reaction equation

HRID 1579129 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-4fd2ce0fc5724637b91340d360e8a081
Source dataset
uspto-grants-1976_01
Patent number
US03930839

Reaction notes

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