Water → 1,1,2-Tribromo-2-(2-benzenesulfonyloxyethyl)cyclopropane

HRID 1265985Notes

Reaction equation

HRID 1265985 reaction equation
[Br:1][C:2]1([Br:9])[CH2:4][C:3]1([Br:8])[CH2:5][CH2:6][OH:7].N1C=CC=CC=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl>[Br:1][C:2]1([Br:9])[CH2:4][C:3]1([Br:8])[CH2:5][CH2:6][O:7][S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 185482081,1,2-Tribromo-2-(2-hydroxyethyl)cyclopropane

Product 1

HCID 865869341,1,2-Tribromo-2-(2-benzenesulfonyloxyethyl)cyclopropaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While cooling a solution of 3.00 g (0.00929 mol) of 1,1,2-tribromo-2-(2-hydroxyethyl)cyclopropane in methylene chloride with 0.901 ml (0.0111 mol) pyridine to 0° C., 1.18 ml (0.00929 mol) of benzene sulfonyl chloride was added dropwise via pipet. Allowed to warm to room temperature. After 3 days, water was added. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 3.10 g of 80% pure 1,1,2-tribromo-2-(2-benzenesulfonyloxyethyl)cyclopropane as an oil.

Workup

  1. customThe resulting mixture was transferred to a separatory funnel
  2. customthe phases were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-a591de9f244b4a9aacb904d9fac8f0a0
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

Loading…