Hydrochloric Acid → 4-Fluoro-2-nitrobenzene-1-sulfonyl chloride

HRID 513372Notes

Reaction equation

HRID 513372 reaction equation
[O:1]=[S:2]([Cl:4])Cl.[N+:5]([C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1N)([O-:7])=[O:6].N([O-])=[O:17].[Na+].Cl>O.Cl[Cu]>[F:15][C:13]1[CH:12]=[CH:11][C:9]([S:2]([Cl:4])(=[O:1])=[O:17])=[C:8]([N+:5]([O-:7])=[O:6])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 677694-Fluoro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27590464-Fluoro-2-nitrobenzene-1-sulfonyl chlorideYield 81.5%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

In a similar fashion using route 3a general procedure 10, SOCl2 (51.4 g, 704 mmol) in water (260 ml), CuCl (0.65 g, 6.4 mmol), 2-nitro 4-fluro-aniline (20 g, 128 mmol), NaNO2 (12.7 g, 184 mmol) and conc. HCl (200 ml) gave the title compound (25 g, 81%) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-f9f7fe10c3c54048bf8df7f10a21fec1
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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