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

HRID 416154Notes

Reaction equation

HRID 416154 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-4a4343ec84ab4cf0a3940188d9b1d1f8
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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