Cesium carbonate → methyl 2-bromo-4-[[(E)-(4-tert-butylphenyl)methylideneamino]oxymethyl]benzoate

HRID 29686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29686
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[Br:12].[C:14]([C:18]1[CH:26]=[CH:25][C:21]([CH:22]=[N:23][OH:24])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:24]/[N:23]=[CH:22]/[C:21]2[CH:25]=[CH:26][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=2)=[CH:6][C:5]=1[Br:12]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamineHCID 19806367Methyl 2-bromo-4-(bromomethyl)benzoate

Produkt 1

HCID 57449661methyl 2-bromo-4-[[(E)-(4-tert-butylphenyl)methylideneamino]oxymethyl]benzoateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

This compound was produced using similar methods as those used in Step 5, example 27, starting with 2-bromo-4-bromomethyl-benzoic acid methyl ester (0.40 g, 1.30 mmol), 4-tert-butyl-benzaldehyde oxime (0.24 g, 1.36 mmol) and cesium carbonate (1.69 g, 5.20 mmol) in acetone (50 mL). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 6/94) to give 2-bromo-4-[({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)methyl]benzoic acid methyl ester (0.43 g, 83%) as a clear, colorless oil. 1H NMR (400 MHz, CDCl3); δ 8.13 (s, 1H), 7.78 (d, 1H), 7.69 (s, 1H), 7.49 (d, 2H), 7.39-7.36 (m, 3H), 5.18 (s, 2H), 3.92 (s, 3H), 1.32 (s, 9H).

Aufarbeitung

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-53ef6fd9f7e04227913d0265f2724142
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

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