5-Bromosalicylic acid → 3'-Chloro-4'-fluoro-4-hydroxy-biphenyl-3-carboxylic acid

HRID 2373782

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[F:8].Br[C:13]1[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([C:18]([OH:20])=[O:19])[CH:21]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

3-Chloro-4-fluoro-phenylboronic acid (3.2 g, 18.4 mmol), 5-bromo-2-hydroxy-benzoic acid (4.0 g, 18.4 mmol), and Pd (PPh3)4 (1.67 g, 1.84 mmol) were dissolved in 250 mL of DME, a 1 M Na2CO3 solution (46 mL, 46.0 mmol) added and the mixture heated to 80° C. for 20 h. The reaction mixture was filtered, partially evaporated and EtOAc (200 mL) and 1 N HCl (100 mL) added. The organic layer washed with 1N HCl and saturated sodium bicarbonate, dried over sodium sulfate, and evaporated. The crude material was filtered through a silica plug (THF) to give 3′-chloro-4′-fluoro-4-hydroxy-biphenyl-3-carboxylic acid (2.15 g).

Aufarbeitung

filtrationThe reaction mixture was filtered
custompartially evaporated
additionEtOAc (200 mL) and 1 N HCl (100 mL) added
washThe organic layer washed with 1N HCl and saturated sodium bicarbonate
dry with materialdried over sodium sulfate
customevaporated
filtrationThe crude material was filtered through a silica plug (THF)

Quellen und Nachweise

ORD-Eintrag: ord-90c5c581e3844ef390a161f7f73dad68
Quelldatensatz: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07459472B2

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