3-Bromobenzaldehyde → 3-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester

HRID 1801212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801212
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([NH2:11])[CH:5]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([N:11]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)[CH:5]=1

Komponenten

5

Edukt 2

HCID 765833-BromobenzaldehydeHCID 52987785Methyl 3-amino-5-chlorobenzoate

Produkt 1

HCID 674427953-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl esterAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture solution of 3-amino-5-chloro-benzoic acid methyl ester (21 g, 113.2 mmol), 3-bromo-benzaldehyde (21 g, 113.2 mmol) and p-toluenesulfonic acid (431 mg, 2.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 3-[(3-bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C15H11BrClNO2 353.62, obsd. (ESI+) [(M+H)+] 351.9 & 353.9.

Aufarbeitung

  1. temperatureto reflux for 12 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-e3cee010114e4b2fa6aae90d07bb0b55
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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