Acetic Acid → Methyl 3-chloro-2-nitrobenzoate

HRID 132381

Reaktionsgleichung

Reaktionsgleichung von HRID 132381
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Si](C=[N+]=[N-])(C)(C)[CH3:15].CC(O)=O>CO.C(#N)C>[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 209023-Chloro-2-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane2×

Produkt 1

HCID 12187125Methyl 3-chloro-2-nitrobenzoateAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21959252Acetonitrile methanolLösungsmittel

Versuchsvorschrift

To 3-chloro-2-nitrobenzoic acid (3.15 g, 15.6 mmol) in methanol/acetonitrile (20 mL/20 mL) was dropwise added TMSCHN2 (2N in hexanes, 11.7 mL, and 23.4 mmol) at 0° C. under N2 over 10 min until the yellow color persist. The mixture was continued stirring for 20 min, followed by dropwise addition of HOAc until the yellow color disappeared to kill excessive TMSCHN2. Partial of the solvent was removed on rotary vacuum, the product came out solution as a light yellow solid, which was filtered and washed with Et2O (2×2 mL) to afford the expected product as a white solid (2.5 g, 74% yield); 1H NMR (400 MHz, CDCl3) δ ppm 3.91 (s, 3 H), 7.51 (t, J=8.06 Hz, 1 H), 7.70 (dd, J=8.06, 1.26 Hz, 1 H), 7.97 (dd, J=7.81, 1.26 Hz, 1 H); Mass spec. 216.02 (MH+), Calc. for C8H6ClNO4 215.00.

Aufarbeitung

  1. customat 0° C.
  2. customover 10 min
  3. customPartial of the solvent was removed on rotary vacuum
  4. filtrationwas filtered
  5. washwashed with Et2O (2×2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-1f9b5ea88ca14387b3af115f17a28767
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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