Iodine → 1-Chloro-4-iodo-2-nitrobenzene
Reaction equation
C(OC(=O)C)(=O)C.[I:8]I.OS(O)(=O)=O.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].[O-]S([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([I:8])=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 64 °C
Procedure
To a jacketed reactor, acetic acid (450 mL) and acetic anhydride (225 mL) is charged at 10° C. Then, to the above mixture, NalO4 powder (97.2 g) and Iodine (77.2 g) is added under stirring. While keep internal temperature at below 30° C., conc. H2SO4 (720 mL) is added dropwise. Then, 2-chloro-nitrobenzene (Rt=11.11 min) is added in one portion, and heat the mixture gradually to 64° C. The resulting mixture continues to be stirred for usually at least 2 hours until process monitor shows almost complete conversion. Then, the mixture is cooled down to room temperature, and transferred slowly into another jacketed reactor with pre-cooled cold Na2SO3 solution (250 g Na2SO3 in 2000 mL water). Collect the wet cake by filtration and wash the cake with water (450 mL×2), then purification of the cake with n-heptane crystallization to afford 2-chloro-5-iodonitrobenzene in 62% yield and 98% HPLC purity (Rt=15.75 min).
Workup
- customat below 30° C.
- stirringto be stirred for usually at least 2 hours until process monitor
- temperatureThen, the mixture is cooled down to room temperature
- customtransferred slowly into another jacketed reactor
- customCollect the wet cake
- filtrationby filtration
- washwash the cake with water (450 mL×2)
- custompurification of the cake
- customwith n-heptane crystallization
Sources & evidence
- ORD record
- ord-132900531a4d4974863db96b64b19da4
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975418B2
Reaction notes
Loading…