Hydrochloric Acid → 3-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-benzoic acid

HRID 1665258

Reaktionsgleichung

C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[F:26])=[CH:14][CH:13]=2)[CH:5]=1.C1COCC1.O.[OH-].[Li+].Cl>O>[F:26][C:19]1[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:27])=[O:2])=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A solution of 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl ester (18.96 g, 50.92 mmol) in inhibitor free THF (100 mL) was treated with a near solution of lithium hydroxide monohydrate (8.4 g, 200.2 mmol) in water (100 mL) at room temperature and heated at 60° C. for 4 h. The reaction mixture was cooled, diluted with water, acidified with aq. 2N HCl and extracted with ethyl acetate. The organic layers were combined, washed with 1/1 water/brine, brine, dried (MgSO4), filtered and concentrated to give 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoic acid (17.89 g, 98.0%) as an off white solid. LC-MS (ES) calculated for C20H13F3O3, 358.32; found m/z 357 [M−H]−.

Aufarbeitung

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washwashed with 1/1 water/brine, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-d28e22108c1b4342b78a2654a05c9e8d
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08039495B2

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