Sodium Carbonate → 2,3',4',5'-Tetrafluorobiphenyl-4-ol

HRID 1797820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797820
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](OB(O)O)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 18180031Water 1,2-dimethoxyethaneHCID 21870694HCID 21870694, Verbindung

Produkt 1

HCID 210521442,3',4',5'-Tetrafluorobiphenyl-4-olAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

At first, 75.0 g of 4-bromo-3-fluorophenol (S3-1), 82.9 g 3,4,5-trifluorophenyl-boric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and the mixture was heated to 80° C. and stirred for 4 hr. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Afterwards, the solution was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent and then dried under reduced pressure. The obtained residue was recrystallized in heptane to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of (S3-3) from (S3-1) was 81.5%.

Aufarbeitung

  1. temperatureNext, the reaction solution was cooled to room temperature
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialAfterwards, the solution was dried over magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customSubsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent
  7. customdried under reduced pressure
  8. customThe obtained residue was recrystallized in heptane

Quellen und Nachweise

ORD-Eintrag
ord-7d4d7f62f4634777a9c312455fa6971e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343595B2

Notizen zur Reaktion

Wird geladen…