Nitric Acid → HCID 86647792, compound

HRID 2091942Notes

Reaction equation

HRID 2091942 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[CH:14]([CH3:16])[CH3:15])(=[O:5])=[O:4].S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[F:18][C:2]([F:17])([F:1])[S:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:24]([O-:26])=[O:25])=[CH:9][C:8]=1[CH:14]([CH3:15])[CH3:16])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 85768909HCID 85768909, compound

Product 1

HCID 86647792HCID 86647792, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-isopropyl-5-methylphenyl trifluoromethanesulfonate (Step 1, 1.3 g, 4.6 mmol) in acetic acid (10 mL) is slowly added conc. sulfuric acid and conc. nitric acid premixed solution (2 mL/0.5 mL) at 0° C. After stifling at room temperature for 2 hours, the mixture is poured into ice water. The mixture is extracted with ethyl acetate (3×20 mL). The combined organic phase is washed with sodium carbonate aqueous solution and brine, and dried over sodium sulfate. After concentration, the crude 2-isopropyl-5-methyl-4-nitrophenyl trifluoromethanesulfonate is used directly in the next step without purification.

Workup

  1. customat 0° C
  2. extractionThe mixture is extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic phase is washed with sodium carbonate aqueous solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration
  6. customthe crude 2-isopropyl-5-methyl-4-nitrophenyl trifluoromethanesulfonate is used directly in the next step without purification

Sources & evidence

ORD record
ord-bf885fa715bf46d792c29b3bffecdd05
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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