Water → 2,3-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

HRID 1269860Notes

Reaction equation

HRID 1269860 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].C(N(CC)CC)C.[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:19][C:18]=1O.O>C(Cl)Cl>[F:1][C:2]([F:8])([F:7])[S:3]([O:6][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[C:22]([CH3:23])[C:17]=1[CH3:16])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2758875TrifluoromethanesulfonateHCID 133312452,3-Dimethyl-4-nitrophenol

Product 1

HCID 229333962,3-Dimethyl-4-nitrophenyl trifluoromethanesulfonateYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous trifluoromethanesulfonate (3.17 ml, 18.8 mmol) and triethylamine (2.75 ml, 19.7 mmol) were added dropwise to a solution of 2,3-dimethyl-4-nitrophenol (3.0 g, 17.9 mmol) in methylene chloride (60 ml) at 0° C. and stirred at room temperature for 1 hour. Then, the reaction solution was poured into water and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 2,3-dimethyl-4-nitrophenyl trifluoromethanesulfonate (5.32 g, 99%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d409822078ca4533832eb0b390a64316
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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