2-Fluoro-4-nitroanisole → 1-Fluoro-4-(isocyanomethyl)-2-methoxy-5-nitrobenzene

HRID 535699

Reaktionsgleichung

Reaktionsgleichung von HRID 535699
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:17][CH3:18].ClC1C=CC(OC[C:26]#[N:27])=CC=1>CN(C=O)C>[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([CH2:1][N+:27]#[C-:26])=[CH:10][C:9]=1[O:17][CH3:18]

Komponenten

5

Edukt 3

HCID 2231042-Fluoro-4-nitroanisoleHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 867126191-Fluoro-4-(isocyanomethyl)-2-methoxy-5-nitrobenzeneAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Potassium t-butoxide (15.74 g, 140 mmol) in DMF (50 mL) was added to a solution of 2-fluoro-1-methoxy-4-nitrobenzene (12 g, 70.1 mmol) and 2-(4-chlorophenoxy)acetonitrile (11.75 g, 70.1 mmol) in DMF (100 mL) at −20° C. The reaction mixture was stirred for 1 h and then quenched with water. The aqueous layer was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 3% ethyl acetate in hexane to afford title compound (3.6 g, 23.21%) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.05 (d, J=10.84 Hz, 1H), 7.27-7.23 (m, 1H), 4.28 (s, 2H), 4.05 (s, 3H); ESI-MS m/z=209 (M−H)−; LCMS Purity: 95%

Aufarbeitung

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2a6c39433ec14587a303ca18ae2bbd43
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859536B2

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