Hydrochloric Acid → 1,1,2-Tribromo-2-(2-hydroxyethyl)cyclopropane

HRID 1265984Notes

Reaction equation

HRID 1265984 reaction equation
[Br:1][C:2]1([Br:14])[CH2:4][C:3]1([Br:13])[CH2:5][CH2:6][O:7]C(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>CO.O>[Br:1][C:2]1([Br:14])[CH2:4][C:3]1([Br:13])[CH2:5][CH2:6][OH:7]

Participants

6

Procedure

To a slurry of 16.5 g (0.0418 mol) of 1,1,2-tribromo-2-[2-(1-ethoxy-ethoxy)-ethyl]-cyclopropane in 145 ml methanol and 40 ml water, was added 0.306 g (0.00161 mol) p-toluene sulfonic acid monohydrate and 145 ml 6M hydrochloric acid. After stirring at room temperature for 1 hour, the solvent was removed from the reaction mixture in vacuo. To the residue, there was added ethyl acetate and water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The isolated organic layer was washed with brine then dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 11.9 g of 1,1,2-tribromo-2-(2-hydroxyethyl)cyclopropane as an oil.

Workup

  1. customthe solvent was removed from the reaction mixture in vacuo
  2. additionTo the residue, there was added ethyl acetate and water
  3. customThe resulting mixture was transferred to a separatory funnel
  4. customthe phases were separated
  5. washThe isolated organic layer was washed with brine
  6. dry with materialthen dried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-de6cfb93a6d846e8bd7627cee35c3a8d
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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