Hydrochloric Acid → 5-Chloro-4-fluoro-2-nitrobenzene-1-sulfonyl chloride

HRID 513370Notes

Reaction equation

HRID 513370 reaction equation
[O:1]=[S:2]([Cl:4])Cl.[Cl:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([CH:12]=1)N.N([O-])=[O:18].[Na+].Cl>O.Cl[Cu]>[Cl:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([S:2]([Cl:4])(=[O:1])=[O:18])[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 5178355-Chloro-4-fluoro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 866697525-Chloro-4-fluoro-2-nitrobenzene-1-sulfonyl chlorideYield 105.3%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

In a similar fashion using route 3a general procedure 10, SOCl2 (2.8 ml, 28.8 mmol) in water (15 ml), CuCl (26 mg, 0.26 mmol), 5-chloro-4-fluoro-2-nitroaniline (1 g, 5.2 mmol), NaNO2 (522 mg, 7.5 mmol) and conc. HCl (10 ml) gave the title compound (1.5 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-6683550bfa624031943e17fa5b3a0d0e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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