1-Bromocyclohex-1-ene → (2-Cyclohexen-1-ylsulfonyl)benzene

HRID 1804762Notes

Reaction equation

HRID 1804762 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1.[Na+].[C:9]1([S:15]([O-:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[CH:7]1([S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 5197751-Bromocyclohex-1-eneHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 4622731(2-Cyclohexen-1-ylsulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Bromocyclohexene (35.9 ml, 310.5 mmol) is dissolved in 1 l of DMF, cooled down to 0° C. and after addition of benzenesulfinic acid sodium salt (86.6 g, 527.8 mmol) the mixture is stirred for 17 h at room temperature. Then the mixture is evaporated under high vacuum. The residue is diluted with ether, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), 1 kg silicagel).

Workup

  1. customThen the mixture is evaporated under high vacuum
  2. additionThe residue is diluted with ether
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), 1 kg silicagel)

Sources & evidence

ORD record
ord-8028d6b3dd8e4feea10725fc703e2bd6
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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