Formic Acid → 2-(4'-Fluorobiphenyl-4-yl)-2-phenylacetic acid

HRID 509179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509179
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:22]([OH:24])=[O:23]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]([OH:24])=[O:23])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 57779630(4'-Fluorobiphenyl-4-yl)(phenyl)methanol

Produkt 1

HCID 577796832-(4'-Fluorobiphenyl-4-yl)-2-phenylacetic acidAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Compound 12 (600 mg, 2.16 mmol) was dissolved in a 25:1 mixture of concentrated sulfuric acid:formic acid (19.76 mL) and left without stirring for 2 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (20-80%) in hexanes to afford compound 13 as an orange oil (40 mg, 6%). 1H NMR (DMSO-d6) δ (ppm): 7.68-7.64 (m, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.40-7.21 (m, 9H), 5.09 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (20-80%) in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-571df04cc54649279b23fb2c5eb47e67
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096565B2

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