Thionyl Chloride → 5-Fluoro-2-nitrobenzene-1-sulfonyl chloride

HRID 513725Notes

Reaction equation

HRID 513725 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8](O)(=[O:10])=[O:9])[CH:7]=1.O=S(Cl)[Cl:17]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8]([Cl:17])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 129043703-Fluoro-6-nitrobenzenesulfonic acid

Product 1

HCID 129043685-Fluoro-2-nitrobenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar fashion using route 39 general procedure 96, 5-fluoro-2-nitro-benzenesulfonic acid 450 (0.6 g, 2.71 mmol), SOCl2 (3.1 ml) and DMF (0.06 ml) at 90° C. for 3 h gave the title compound (3.4 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Workup

  1. customat 90° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-c32e5e7874b341e3886b6cef63e5ae9f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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