Methanesulfonic Acid → HCID 14026543, compound

HRID 1814657Notes

Reaction equation

HRID 1814657 reaction equation
S(Cl)(Cl)=O.[CH3:5][S:6](O)(=[O:8])=[O:7].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([O-:12])=[O:11].FC(F)(F)S(O)(=O)=O>C(OCC)(=O)C.O>[CH3:5][S:6]([C:17]1[CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[CH:15][C:16]=1[CH3:19])(=[O:8])=[O:7]

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 74734-NitrotolueneHCID 24386Thionyl ChlorideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 14026543HCID 14026543, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, thionylchloride (4 ml, 58 mmol) and methanesulphonic acid (9 mL, 146 mmol) were refluxed for 90 min. 4-Nitrotoluene (4 g, 29 mmol) and triflouromethanesulphonic acid (200 uL, 3 mmol) were added and the mixture was allowed to stand for 48 hours at 120° C. The mixture was cooled to 0° C. and water (50 mL) was carefully added, followed by addition of ethyl acetate (150 mL). The organic phase was separated and extracted with a saturated solution of sodium hydrogencarbonate (2×50 mL) and water (2×50 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (heptane/ethylacetate, 1:1) to give 0.75 g of 2-methylsulfonyl-1-methyl-4-nitrobenzene.

Workup

  1. customThe organic phase was separated
  2. extractionextracted with a saturated solution of sodium hydrogencarbonate (2×50 mL) and water (2×50 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (heptane/ethylacetate, 1:1)

Sources & evidence

ORD record
ord-9462c71695b6407e9e978ccac337fd7a
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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