Ethyl Acetate → 3-Fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenol

HRID 452467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452467
[F:1][C:2]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:8]([OH:16])[C:3]=1[C:4](OC)=[O:5].[Li+].[BH4-].CCOC(C)=O>C1COCC1>[F:1][C:2]1[C:3]([CH2:4][OH:5])=[C:8]([OH:16])[CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 66887484Methyl 2-fluoro-6-hydroxy-4-(methylsulfonyl)benzoate

Produkt 1

HCID 668875163-Fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenolAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-fluoro-6-hydroxy-4-(methylsulfonyl)benzoate (0.14 g, 0.57 mmol) was dissolved in THF (dry) (5 ml). LiBH4 (2M in THF) (0.57 ml, 1.14 mmol) was added dropwise under nitrogen at 0° C. The mixture was allowed to warm to RT and stirred under nitrogen for 45 min. EtOAc was added and the mixture was further quenched with MeOH, then water. The mixture was acidified with 1N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to give the crude title compound (0.12 g) 1H-NMR (400 MHz, CD3OD): δ 7.20 (1H, s), 7.16 (1H, dd, J 8.4, 2), δ 4.73 (2H, d, J 1.6), δ 3.10 (3H, s) ppm (J-values are in Hz and shifts relative to solvent-peak at 3.31 ppm).

Aufarbeitung

  1. customthe mixture was further quenched with MeOH
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6ee9932b9cff4c48ae2eea209764fc2e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492372B2

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