Acetone → Nitrobenzene

HRID 2081518Notes

Reaction equation

HRID 2081518 reaction equation
O[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC(C)=O.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CN(C=O)C>[N+:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

The intermediate nitrobenzenes with the alkoxycarbonylalkoxy W substituent are formed from 2-hydroxy-4-fluoronitrobenzene. 2-Hydroxy-4-fluoronitrobenzene is reacted with a haloalkylcarboxylate (e.g., ethyl 2-bromopropionate) in a suitable solvent (e.g., acetone, acetonitrile, DMF, or DMSO) in the presence of a base (e.g., potassium carbonate) for an extended period (e.g., 3 days). The intermediate nitrobenzene is then isolated by standard laboratory techniques.

Sources & evidence

ORD record
ord-e6990cdb59984620b8581a2f7dabc30e
Source dataset
uspto-grants-1993_02
Patent number
US05185025

Reaction notes

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