4-Bromophenol → 4-(2,3-Difluorophenyl)phenol

HRID 1289375

Reaktionsgleichung

Reaktionsgleichung von HRID 1289375
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(COC)OC.C(=O)([O-])[O-].[Cs+].[Cs+]>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.O>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 78084-BromophenolHCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2734333(2,3-Difluorophenyl)boronic acid

Produkt 1

HCID 189208344-(2,3-Difluorophenyl)phenolAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

First, 34.6 g of 4-bromphenol, 37.9 g of 2,3-difluorophenylboronic acid, 380 ml of dimethoxyethane, 380 ml of water, 97.8 g of cesium carbonate, and 7 g of tetrakis(triphenylphosphine)palladium were placed in a 1 L flask. The mixture was stirred under reflux for 20 hours. The reaction mixture was poured into water and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1) and recrvstallized from hexane to obtain 30.9 g of 2,3-difluoro-4'-hydroxybiphenyl (Y: 75%). The compound thus obtained had a purity of 99.8% by GC and an m.p. of 132° C. to 134.4° C.

Aufarbeitung

  1. temperatureunder reflux for 20 hours
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-7a826045604c4a2db7210bd703efeeed
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750213

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