Isopropanol → Propan-2-yl 4-iodobenzoate
Reaction equation
S(Cl)(Cl)=O.[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1.[CH:15](O)([CH3:17])[CH3:16]>>[CH:15]([O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([I:5])=[CH:7][CH:8]=1)([CH3:17])[CH3:16]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
Thionyl chloride (1.4 ml) was added to a solution of 4-iodobenzoic acid (3.72 g) in isopropanol (25 ml) and the reaction mixture heated at 50° C. for several hours. The reaction mixture was cooled to ambient temperature and evaporated. Methylene chloride was added to the residue and the mixture filtered. The filtrate was washed with saturated sodium bicarbonate solution, water, saturated brine, dried (MgSO4) and evaporated to give isopropyl-4-iodo-benzoate as an oil (1.5 g); NMR: 1.28-137(6H,d), 5.04-5.21(1H,m), 7.65-7.74(2H,d), 7.88-7.95(2H,d); m/z 291(M+H).