Hydrochloric Acid → 1-(4'-Bromo-2'-fluorobiphenyl-4-yl)propan-1-one

HRID 1755614

Reaktionsgleichung

Reaktionsgleichung von HRID 1755614
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([F:18])[CH:7]=1.[C:19](Cl)(=[O:22])[CH2:20][CH3:21].Cl>C(=S)=S>[F:18][C:8]1[CH:7]=[C:6]([Br:5])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 8220021-(4'-Bromo-2'-fluorobiphenyl-4-yl)propan-1-oneAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

40 g of aluminum chloride and 280 ml of carbon disulfide were taken into a flask, cooled with an ice-salt bath to 0° C. or lower and stirred. A solution of 70 g of 4-bromo-2-fluorobiphenyl as dissolved in 180 ml of carbon disulfide was dropwise added thereto. A solution of 26 g of propionic acid chloride as dissolved in 100 ml of carbon disulfide was dropwise added thereto at 0° C. or lower. After addition, the whole was stirred for 2 hours at 0° C. or lower and then at room temperature overnight. After reaction, the reaction solution was poured into 30 ml of concentrated hydrochloric acid and 300 g of ice and extracted with chloroform. The organic layer was washed three times with water, two times with an aqueous 2% sodium hydroxide solution and then three times with water, and chloroform and carbon disulfide were removed by distillation. The residue was recrystallized from a mixed solvent comprising acetone and methanol to obtain 29 g of 2-fluoro-4-bromo-4'-propionylbiphenyl.

Aufarbeitung

  1. additionwas dropwise added
  2. additionwas dropwise added
  3. customat 0° C.
  4. additionAfter addition
  5. stirringthe whole was stirred for 2 hours at 0° C.
  6. customat room temperature
  7. customovernight
  8. customAfter reaction
  9. extractionextracted with chloroform
  10. washThe organic layer was washed three times with water, two times with an aqueous 2% sodium hydroxide solution
  11. customthree times with water, and chloroform and carbon disulfide were removed by distillation
  12. customThe residue was recrystallized from a mixed solvent comprising acetone and methanol

Quellen und Nachweise

ORD-Eintrag
ord-46859a31ab31461b95d8d0e940c1bb9c
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05437815

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