Benzyl Alcohol → 1-(Benzyloxy)-3-fluoro-2-methyl-4-nitrobenzene

HRID 2042068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042068
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[CH3:12].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:13]([O:20][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 127954862,6-Difluoro-3-nitrotoluene

Produkt 1

HCID 667290181-(Benzyloxy)-3-fluoro-2-methyl-4-nitrobenzeneAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1,3-difluoro-2-methyl-4-nitrobenzene (16 g, 0.092 mol), benzyl alcohol (10 g, 0.092 mol) and K2CO3 (25.3 g, 0.18 mol) were combined in DMF (250 mL) and heated to 100° C. overnight. The mixture was poured into water and extracted with EtOAc (3×200 mL). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by column chromatography on silica gel to give 1-benzyloxy-3-fluoro-2-methyl-4-nitrobenzene (8 g, 33% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.04 (t, J=8.8 Hz, 1H), 7.30-7.46 (m, 5H), 7.08 (d, J=9.2 Hz, 1H), 5.28 (s, 2H), 2.13 (s, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9c889fea8fdf461a8fda2874d4fb3dad
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586565B2

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