Triethylamine → 4-Cyano-2-methoxyphenyl trifluoromethanesulfonate

HRID 871979Notes

Reaction equation

HRID 871979 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([O:9][CH3:10])[CH:8]=1)#[N:2].C(N(CC)CC)C.[F:19][C:20]([F:26])([F:25])[S:21](Cl)(=[O:23])=[O:22].C(OCC)(=O)C>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][S:21]([C:20]([F:26])([F:25])[F:19])(=[O:23])=[O:22])=[C:7]([O:9][CH3:10])[CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 781354-Hydroxy-3-methoxybenzonitrileHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 166592584-Cyano-2-methoxyphenyl trifluoromethanesulfonateYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 5-cyano-2-hydroxyanisole (600 mg, 4.02 mmol) and triethylamine (1.40 mL, 10.0 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) under argon atmosphere. Trifluoromethanesulfonyl chloride (642 μL, 6.03 mmol) were added thereto at −10° C., and stirred at the same temperature for 1 hour. Ethyl acetate (100 mL) and water (100 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (979 mg) as a colorless solid. (Yield 87%)

Workup

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6612030265264d4f9a4a6f5ef34e582f
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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