Benzaldehyde → 20534-67-2

HRID 1871074Notes

Reaction equation

HRID 1871074 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].C(=O)C1C=CC=CC=1.N#N>Cl[Pd]Cl.C(N(CC)CC)C>[CH:1](=[N:14][C:13]1[CH:12]=[C:11]([Br:10])[CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 947NitrogenHCID 115623-Bromoaniline

Product 1

HCID 52554820534-67-2

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8471TriethylamineSolvent

Procedure

To a nitrogen purged 250 mL three-neck flask equipped with a mechanical stirrer, reflux condenser and septum inlet was added benzoic acid (300 mg, 2.8 mmol) and PdCl2 (25 mg). Then 3-bromoaniline (25 g, 145 mmol), benzaldehyde (4.6 g, 44 mmol) and triethylamine (80 mL) were charged. The resulting mixture was vacuum deaerated (150 torr; N2 backfill; 5x) and heated under nitrogen at reflux for one hour to form the N-benzylidene 3-aminophenylbromide.

Workup

  1. customTo a nitrogen purged 250 mL three-neck flask
  2. customequipped with a mechanical stirrer
  3. temperaturereflux condenser and septum inlet
  4. temperatureat reflux for one hour

Sources & evidence

ORD record
ord-986f4b606b124b33915b58efeced0faa
Source dataset
uspto-grants-2000_08
Patent number
US06100429

Reaction notes

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