3,5-Dichloroaniline → 4-Bromo-2-{[(3,5-dichlorophenyl)imino]methyl}phenol

HRID 421014

Reaction equation

HRID 421014 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[NH2:15]>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[N:15]=[CH:7][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[OH:10]

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7101644-Bromo-2-{[(3,5-dichlorophenyl)imino]methyl}phenolYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromosalicylaldehyde (1.01 g, 5 mmol), 3,5-dichloroaniline (810 mg, 5 mmol) and ethanol (25 mL) was refluxed for 1 hour under argon atmosphere. After the reaction mixture was cooled to room temperature, the separated crystal was filtered to give 3,5-dichloro-N-(5-bromo-2-hydroxybenzylidene)aniline (1.52 g, 88.2%) as an orange crystal.

Workup

  1. temperaturewas refluxed for 1 hour under argon atmosphere
  2. filtrationthe separated crystal was filtered

Sources & evidence

ORD record
ord-fee8b1d6fff14516b2d00f63bf930981
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Linked notes

Loading…