1-Bromocyclohex-1-ene → (2-Cyclohexen-1-ylsulfonyl)benzene
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).