Sodium Carbonate → 3-Chloro-5'-fluoro-2'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

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Reaktionsgleichung

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17](B(O)O)[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[C:13]([F:12])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

4-Bromo-2-chlorobenzoic acid (1.1 g) and 5-fluoro-2-methoxyphenylboronic acid (0.94 g) were suspended in toluene (20 mL) and ethanol (20 mL). Aqueous 2M sodium carbonate solution (16 mL) and tetrakis(triphenylphosphine) palladium(0) (0.14 g) were added and the reaction was heated at 95° C. for 20 h. The mixture was diluted with water, extracted with diethyl ether (discarded). The aqueous layer was acidified with aqueous 2M hydrochloric acid, extracted with ethyl acetate, dried (MgSO4) and concentrated under reduced pressure to give the sub titled product as a cream solid (1.25 g).

Aufarbeitung

extractionextracted with diethyl ether (discarded)
extractionextracted with ethyl acetate
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-db53b110bdac418ab14badacf7bf4aa3
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08507544B2

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