2-(2-Nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid, ammonium salt → 2-(2-Amino-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid

HRID 1416349Notes

Reaction equation

HRID 1416349 reaction equation
[NH4+].[N+:2]([C:5]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:6]=1[O:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:9]=1[S:16]([O-:19])(=[O:18])=[O:17])([O-])=O>C(O)(=O)C.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:2][C:5]1[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:6]=1[O:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:9]=1[S:16]([OH:19])(=[O:18])=[O:17]

Participants

5

Reactant 1

HCID 154073272-(2-Nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid, ammonium salt

Product 1

HCID 152858292-(2-Amino-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The 2-(2-nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid, ammonium salt (5 g, 11.2 mmol) was dissolved in acetic acid (75 mL). The mixture was diluted with water (75 mL), and a 20% aqueous solution of titanium trichloride (65 mL) was added. After aqueous workup the crude product was flash chromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide) to give the title compound. 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 6.94 (dd, 1H),6.87 (s, 1H).

Workup

  1. customchromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-3fbc94e16bf64b58a1491f91d05ade6c
Source dataset
uspto-grants-1999_06
Patent number
US05912270

Reaction notes

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