Sulfuryl chloride → 2-Chloro-1-(4-chloro-2-fluorophenyl)ethan-1-one

HRID 597866Notes

Reaction equation

HRID 597866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.S(Cl)([Cl:15])(=O)=O>CO>[Cl:15][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:11])=[O:10]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 150305521-(4-Chloro-2-fluorophenyl)ethan-1-one

Product 1

HCID 450810122-Chloro-1-(4-chloro-2-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of heptanes (1.5 L), methanol (0.4 L), and 1-(4-chloro-2-fluorophenyl)ethanone (1 kg, 5.81 mol) with cooling to <5° C. Add sulfuryl chloride (0.608 L, 1.02 kg, 7.55 mol) as a heptanes (1.5 L) solution drop-wise to the mixture keeping the reaction temperature <15° C. during the addition. After 2 h quench the reaction at ambient temperature to a pH of 6 with sodium hydroxide (5N, 2.0 L). Extract the reaction mixture with methylene chloride (2 L) and concentrate the extract to form a white solid. Filter and dry the solid.

Workup

  1. temperaturewith cooling to <5° C
  2. customthe reaction temperature <15° C.
  3. additionduring the addition
  4. customAfter 2 h quench
  5. customthe reaction at ambient temperature to a pH of 6 with sodium hydroxide (5N, 2.0 L)
  6. extractionExtract the reaction mixture with methylene chloride (2 L)
  7. concentrationconcentrate the
  8. extractionextract
  9. customto form a white solid
  10. filtrationFilter
  11. customdry the solid

Sources & evidence

ORD record
ord-2502cf4b6825433e90c5fd89af44f7b1
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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