HCID 86740721, compound → 1-Chloro-2-nitrobenzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].ClC(C)C([O-])=O.CN(C=O)C>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]Participants
Reagents, catalysts & solvents 1
Procedure
Example VI was repeated except that the 2-chloronitrobenzene/2-chloropropionate/DMF solution was added over a period of 30 minutes during which the temperature of the reaction mixture was maintained at 25°-30° C. by intermittent cooling with an ice/water bath, and stirring of the reaction mixture was continued for 30 minutes after completion of this dropwise addition. The reaction mixture was then poured into 150 ml of 1N HCl and extracted with four 150 ml portions of diethyl ether. The ether layers were combined, dried over MgSO4, and concentrated to give an oil which was adsorbed on 15 g of silica gel (230-400 mesh). This was loaded on a column of 200 g of silica gel which was eluted with 30% dichloromethane/70% petroleum ether under nitrogen pressure to give 0.65 g of unreacted 2-chloronitrobenzene and 8.4 g of methyl 2-(3-chloro-4-nitrobenzene)propionate--a yield of about 68%.
Workup
- additionwas added over a period of 30 minutes during which the temperature of the reaction mixture
- temperaturewas maintained at 25°-30° C.
- temperatureby intermittent cooling with an ice/water bath
- additionafter completion of this dropwise addition
- extractionextracted with four 150 ml portions of diethyl ether
- dry with materialdried over MgSO4
- concentrationconcentrated
- customto give an oil which
- washwas eluted with 30% dichloromethane/70% petroleum ether under nitrogen pressure
Sources & evidence
- ORD record
- ord-c8fceb63bcdf4145a6bf9c1c3960bea4
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581463
Reaction notes
Loading…