Sodium Hydroxide → 2',6'-Dichloro-5-fluoro-2-methoxybiphenyl

HRID 902319

Reaktionsgleichung

Reaktionsgleichung von HRID 902319
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1Br.[OH-].[Na+].[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17](B(O)O)[CH:18]=1>COCCOC.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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:15]1[CH:14]=[C:13]([F:12])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 295681-Bromo-2,6-dichlorobenzeneHCID 27826735-Fluoro-2-methoxyphenylboronic acid

Produkt 1

HCID 586469552',6'-Dichloro-5-fluoro-2-methoxybiphenylAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2,6-dichlorobromobenzene (3.5 g, 15.7 mmol) and sodium hydroxide (3.14 g, 78.5 mmol) in DME-water (2:1) was added 5-fluoro-2-methoxybenzene boronic acid (4.0 g, 23.5 mmol) at 90° C., followed by tetrakis(triphenylphosphine)palladium (0) (0.9 g, 0.78 mmol). The reaction mixture was heated at 90° C. overnight and cooled to room temperature. The mixture was extracted with methylene chloride and washed with water. The organic solvent was removed under vacuum. Chromatography with 5% ethyl acetate in hexanes afforded 2.62 g (87%) of 2′,6′-dichloro-5-fluoro-2-methoxybiphenyl as a colorless oil. MS (EI) m/z 270 (M+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with methylene chloride
  3. washwashed with water
  4. customThe organic solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2542c6f5ef0c48458405b2ca8702a00d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365095B2

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