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

HRID 1416348Notes

Reaction equation

HRID 1416348 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[N+:6]([C:9]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:10]=1[O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][CH:13]=1)([O-:8])=[O:7]>C(Cl)Cl>[NH4+:6].[N+:6]([C:9]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:10]=1[O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=1[S:1]([O-:3])(=[O:5])=[O:2])([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13430092-(2-Nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fuming sulfuric acid (8 mililiter (hereinafter mL) was cooled to -20° C. and 2-(2-nitro-4-trifluoromethyl-phenoxy)-4,5-dichlorobenzene (8 g, 22.8 mmol) in methylene chloride (8 mL) was added to the solution. The mixture was stirred for 15 min and then quenched in ice. Extraction with ethyl acetate followed by flash chromatography (silica gel, methylene chloride/isopropanol/ammonium hydroxide) gave the title compound. 1H NMR (400 MHz, CD3OD) δ 8.31 (d, 1H), 8.11 (s, 1H), 7.87 (dd, 1H), 7.4 (s, 1H), 7.16 (d, 1H )

Workup

  1. customquenched in ice
  2. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-c2f57e38277c43948951732ae78fcef5
Source dataset
uspto-grants-1999_06
Patent number
US05912270

Reaction notes

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