Hydrochloric Acid → 3'-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

HRID 1165729

Reaktionsgleichung

Reaktionsgleichung von HRID 1165729
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])C.Br[O-].[Na+].S([O-])(O)=[O:23].[Na+].Cl>O1CCOCC1>[F:18][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:23])=[CH:5][CH:6]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 143886483'-Fluoro-4'-methoxy-4-acetylbiphenylHCID 23665763Sodium BisulfiteHCID 23673712Sodium hypobromite2×

Produkt 1

HCID 12031663'-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-carboxylic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The resulting 4-acetyl-3'-fluoro-4'-methoxybiphenyl (7.2 g) was dissolved in 300 ml of dioxane, and 360 ml of a solution of sodium hypobromite (prepared from 75 g of sodium hydroxide and 78 g of bromine) was added over about 40 minutes at 0° to 5° C., and the mixture was stirred at 30° to 35° C. for 2 hours. The excess of sodium hypobromite was decomposed with a saturated aqueous solution of sodium hydrogen sulfite, and 10% hydrochloric acid was added to adjust the pH of the solution to 3 to 4. The solution was left to stand at 10° C. for 20 hours to permit crystallization. The resulting crystals were filtered to give 7.2 g of 3'-fluoro-4'-methoxybiphenyl-4-carboxylic acid. Recrystallization from isopropyl alcohol gave 6.8 g of the desired product. Yield 94%.

Aufarbeitung

  1. additionwas added
  2. waitThe solution was left
  3. waitto stand at 10° C. for 20 hours
  4. customcrystallization
  5. filtrationThe resulting crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-3c7883a9af13498d9053b98706365e93
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04911862

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