Sodium Thiosulfate → 4-Bromo-2-fluoro-3,5-dimethylphenol

HRID 453430Notes

Reaction equation

HRID 453430 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[O-]S(C(F)(F)[F:16])(=O)=O.F[N+]1C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([F:16])[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 819704-Bromo-3,5-dimethylphenolHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)

Product 1

HCID 593425984-Bromo-2-fluoro-3,5-dimethylphenolYield 36.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (2.00 g, 9.95 mmol) in 1,2-dichloroethane (20 mL) was added N-fluoropyridinium triflate (6.15 g, 24.9 mmol), and the mixture was heated under reflux for 7 hr. The reaction mixture was treated with 1 M aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.790 g, yield 36%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

Sources & evidence

ORD record
ord-c6b0ce29acba4d0199cd8c36bc85c3b6
Source dataset
uspto-grants-2013_07
Patent number
US08492430B2

Reaction notes

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