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

HRID 129874

Reaction equation

HRID 129874 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) δ8.02 (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-e89d138d903a404787e211e625b60ee4
Source dataset
uspto-grants-1995_11
Patent number
US05470882

Linked notes

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