p-Fluoronitrobenzene → 2-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzene

HRID 2292272Notes

Reaction equation

HRID 2292272 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]1([S:17]([CH2:20]Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH2:20][S:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])=[O:18])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 81625((Chloromethyl)sulphonyl)benzene

Product 1

HCID 131807962-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-nitro-fluorobenzene and phenylsulfonylmethyl chloride were reacted in dimethylsulfoxide in the presence of potassium tert.-butylate to form 4-nitro-3-(phenylsulfonylmethyl)-fluorobenzene which was reacted with N-hydroxy-phthalimide to form 0-[4-nitro-3-(phenylsulfonylmethyl)-phenoxy]-phthalimide which was reacted to obtain 0-[4-nitro-3-phenylsulfonylmethyl)-phenyl]-hydroxylamine melting at 195°-196° C.

Sources & evidence

ORD record
ord-f4f8dfd778c44d438da3e3a28d133030
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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