4-Chlorobutyryl chloride → 4-Chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone

HRID 1764896Notes

Reaction equation

HRID 1764896 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH3:9])[CH:3]=1.[Cl:10][CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Cl:10][CH2:11][CH2:12][CH2:13][C:14]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[S:8][CH3:9])=[O:15]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 27591643-FluorothioanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 227354674-Chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanoneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystallized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal.

Workup

  1. customthen quenched by addition of H2O
  2. extractionextracted with Et2O
  3. washThe combine organic solution was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting white solid was recrystallized

Sources & evidence

ORD record
ord-86b15dbadcab4411a8342153b93059ce
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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