1-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanone → 4-(4-Fluorophenyl)benzoic acid

HRID 2101232

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])C)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[O:17](Br)[Na].C(O)(=O)C.C1(C2C=CC=CC=2)C=CC=CC=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:17])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

NaOH (7 g) was dissolved in water (25 mL) and cooled in an ice bath. Bromine (7.8 g) was added dropwise to give a solution of NaOBr. 1-(4′-Fluoro-biphenyl-4-yl)-ethanone (0.01 mol) was dissolved in dioxane (35 mL) and warmed to 50° C. in a water bath. The NaOBr solution was added slowly to the stirred solution of the biphenyl acetate and stirring continued at 50° C. for a further 20 minutes. The solution was allowed to cool and a solution of sodium metabisulphite (8 g in 40 mL water) was added followed by water (170 mL). 50 mL of the liquid was evaporated under reduced pressure with heating. The remainder was acidified with HCl (5 mL) and a white precipitate formed upon cooling. The precipitate was filtered and recrystallised from acetic acid to give the title compound. δC (CDCl3, 62.9 MHz): 115.9, 126.8, 129.2, 129.6, 129.8 (d, J 2.9), 135.5 (d, J 2.9), 143.2, 162.4 (d, J 245.1) and 167.2.

Aufarbeitung

temperatureto cool
custom50 mL of the liquid was evaporated under reduced pressure
temperaturewith heating
customa white precipitate formed
temperatureupon cooling
filtrationThe precipitate was filtered
customrecrystallised from acetic acid

Quellen und Nachweise

ORD-Eintrag: ord-f4e8cebf7e8249d6b95b7196fbd0c0bd
Quelldatensatz: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07572825B2

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