Thionyl Chloride → HCID 19825181, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:15][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([OH:12])[CH2:9][CH2:10][CH3:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4.0 g (17.5 mmol) of 1-(3-bromophenyl)-butanol is stirred with 4 ml of thionyl chloride for 1 hour at room temperature. 10 ml of toluene is added to the reaction mixture. 1-Chloro-1-(3-bromophenyl)-butanol is obtained after concentration by evaporation in a vacuum. 1.3 g of imidazole is dissolved in 20 ml of dimethylformamide and mixed with 0.6 g of sodium hydride (80% in oil) under argon protective gas atmosphere. It is stirred for 1 hour at room temperature. The chlorine compound is instilled into 15 ml of dimethylformamide and allowed to stand overnight. The mixture is precipitated in 200 ml of water and extracted with ethyl acetate. The organic phase is concentrated by evaporation in a vacuum and then distilled on a bulb tube at 150° C./0.03 mbar. 1.6 g of 1-[1-(3-bromophenyl)-butyl]-imidazole is obtained as a viscous oil.
Sources & evidence
- ORD record
- ord-5df55939a11e4d03bdbe26c1f91a06cd
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05045558
Reaction notes
Loading…