3-Bromobenzaldehyde → 4-[(3-Bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester

HRID 2045415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045415
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([Cl: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]=[CH:8][C:7]([N:10]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)=[C:6]([Cl:11])[CH:5]=1

Komponenten

5

Edukt 2

HCID 765833-BromobenzaldehydeHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Produkt 1

HCID 674417354-[(3-Bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl esterAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture solution of 4-amino-3-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 4-[(3-bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C18H11BrClNO2 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-f51a73525c4247bd870b77fa5658b24c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586747B2

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