Water → 1-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

HRID 1023850Notes

Reaction equation

HRID 1023850 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.S(Cl)([Cl:15])(=O)=O.O>C(O)(=O)C>[Cl:15][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:11])=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=1.[Cl:15][C:3]1[C:4]([OH:11])=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 2

HCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanoneHCID 672052361-(3-Chloro-4-fluoro-2-hydroxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To 1-(4-fluoro-2-hydroxyphenyl)ethanone (1.7 g, 11.03 mmol) in glacial acetic acid (24 mL) at 10° C. was slowly added sulfuryl chloride (2.23 g, 16.54 mmol). The mixture was heated to 120° C. and was allowed to stir for overnight. The solution was cooled down to room temperature and poured into water (30 mL). The water layer was extracted with EtOAc for three times. The EtOAc was washed with satd. Aq NaHCO3, water, brine, dried (Na2SO4) and concentrated recrystallized The mix was purified by column chromatography using 1:10 Hexanes:Ethyl acetate to yield 234 mg of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone and 400 mg of 1-(3-chloro-4-fluoro-2-hydroxyphenyl)ethanone. These compounds were used in the next step without characterization.

Workup

  1. customat 10° C.
  2. temperatureThe solution was cooled down to room temperature
  3. extractionThe water layer was extracted with EtOAc for three times
  4. washThe EtOAc was washed with satd
  5. dry with materialAq NaHCO3, water, brine, dried (Na2SO4)
  6. concentrationconcentrated
  7. customrecrystallized The mix
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-291ab45ed0594c0eb9c6f024e2e881dc
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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