Hydrochloric Acid → 2-Nitro-4-trifluoromethoxy-benzenesulfonyl chloride

HRID 513373Notes

Reaction equation

HRID 513373 reaction equation
[O:1]=[S:2]([Cl:4])Cl.[N+:5]([C:8]1[CH:14]=[C:13]([O:15][C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1N)([O-:7])=[O:6].Cl.N([O-])=[O:22].[Na+]>O.Cl[Cu]>[N+:5]([C:8]1[CH:14]=[C:13]([O:15][C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[S:2]([Cl:4])(=[O:1])=[O:22])([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 27757722-Nitro-4-(trifluoromethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 866697542-Nitro-4-trifluoromethoxy-benzenesulfonyl chlorideYield 105.4%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

In a similar fashion using route 3a general procedure 10, SOCl2 (0.36 ml, 4.95 mmol) in cold water (2 ml), CuCl (5 mg, 0.05 mmol), 2-nitro-4-(trifluoromethoxy)aniline (200 mg, 0.90 mmol), conc. HCl (2 ml), NaNO2 (90 mg, 1.3 mmol) in water (2 ml) gave the title compound (290 mg) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-1e0fd975f5f94606babf2e5cfa5654ae
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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