7-Bromo-3-methylnaphthalen-1-ol → 1-Naphthol, 3-methyl-

HRID 926203

Reaktionsgleichung

Reaktionsgleichung von HRID 926203
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1>[Pd].CCO>[CH3:13][C:7]1[CH:8]=[C:9]([OH:12])[C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[CH:2][CH:11]=2

Komponenten

4

Edukt 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

Produkt 1

HCID 261351-Naphthol, 3-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A slurry of 7-bromo-3-methylnaphthalen-1-ol (100 mg, 0.421 mmol), 10% w/w Pd/C (45 mg, 42.1 μmol Pd), and absolute EtOH (2.0 mL) was purged under vacuum and backfilled with H2 from a balloon several times. The suspension was stirred under a balloon of H2 at 23° C. overnight. The reaction was filtered over Celite, the cake was washed with EtOAc. The filtrate was concentrated and dissolved in DCM. The solution was loaded onto a 12 g “gold” ISCO silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=7.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.47-7.39 (m, 2H), 7.22 (s, 1H), 6.67 (s, 1H), 2.45 (s, 3H).

Aufarbeitung

  1. filtrationThe reaction was filtered over Celite
  2. washthe cake was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in DCM
  5. custompurified by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3ce10ff026c24790bc283c48f3f74460
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284323B2

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