Ethyl Acetate → 4-Bromo-3,5-dimethylphenyl trifluoromethanesulfonate

HRID 1043929Notes

Reaction equation

HRID 1043929 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20](O)=[CH:19][C:18]=1[CH3:25].C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:20]1[CH:21]=[C:22]([CH3:23])[C:17]([Br:16])=[C:18]([CH3:25])[CH:19]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 579788384-Bromo-3,5-dimethylphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (2.0 mL) was added dropwise to a solution of 4-bromo-3,5-dimethylphenol (CAS No. 7463-51-6) (2.0 g) and TEA (1.94 mL) in DCM (20 mL) under ice-cooling over three minutes. The reaction mixture was stirred at room temperature for 30 minutes. Ice and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The organic layer was sequentially washed with 1 N hydrochloric acid, water, a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5%) to give the title compound (3.20 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5%)

Sources & evidence

ORD record
ord-071f964e3f004e07af1c46664ab35a03
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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