Acetic Acid → 2-Fluoro-5-hydroxybenzoic acid

HRID 714116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714116
[F:1][C:2]1C=[CH:8][C:7]([O:10]C)=[CH:6][C:3]=1C#N.[C:12]([OH:15])(=[O:14])[CH3:13]>Br.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:6][C:7]([OH:10])=[CH:8][C:13]=1[C:12]([OH:15])=[O:14]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 27745462-Fluoro-5-methoxybenzonitrile

Produkt 1

HCID 27744802-Fluoro-5-hydroxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Fluoro-5-methoxybenzonitrile (3d, purchased from Alfa Aesar) (5 g, 33 mmol) was dissolved in hydrobromic acid (50 mL) and glacial acetic acid (30 mL), refluxed for 28 hours at 140° C., and then the reaction mixture was diluted with 100 mL ethyl acetate. The reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times. The organic layers were combined and concentrated to give a crude product of 2-fluoro-5-hydroxybenzoic acid (3e), 2.88 g white solid (yield 56%). 1H NMR (600 MHz, DMSO-d6) δ 7.19-7.17 (m, 1H), 7.08-7.04 (m, 1H), 6.95-6.92 (m, 1H); ESI-MS m/z: calculated for 156.02. found 154.91 [M−H]+.

Aufarbeitung

  1. washThe reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-033fb64703a748a7b4d1e111c3f5a333
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187430B2

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