Water → Methyl 4-chloro-3-methoxy-5-nitrobenzoate

HRID 62754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62754
O[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].C(Cl)(=O)C([Cl:20])=O.O>CN(C=O)C>[Cl:20][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 10878886Methyl 4-hydroxy-3-methoxy-5-nitrobenzoate

Produkt 1

HCID 49757533Methyl 4-chloro-3-methoxy-5-nitrobenzoateAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of methyl 4-hydroxy-3-methoxy-5-nitrobenzoate (2) (4.4 g, 19 mmol) in DMF (30 mL) at 0° C. was treated with oxalyl chloride (5.09 mL, 58.1 mmol) dropwise. The mixture was then stirred at 80° C. for 3 h under a CaCl2 drying tube. The mixture was allowed to cool to RT, poured in to iced water (100 mL) and stirred for 15 min. The precipitate was collected by filtration and washed with water and MeOH to afford methyl 4-chloro-3-methoxy-5-nitrobenzoate (3) (3.2 g, 65% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ: 8.04 (1H, d), 7.77 (1H, d), 4.04 (3H, s), 3.97 (3H, s).

Aufarbeitung

  1. temperatureto cool to RT
  2. stirringstirred for 15 min
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and MeOH

Quellen und Nachweise

ORD-Eintrag
ord-21e65c90f3d64840828314bc29c0f638
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447028B2

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