5-Bromo-2-nitrovanillin → HCID 14936539, compound

HRID 576382Notes

Reaction equation

HRID 576382 reaction equation
[Br:1][C:2]1[C:3]([OH:15])=[C:4]([O:13][CH3:14])[C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[CH:7]=[O:8]>CCO.O.[Fe]>[NH2:10][C:5]1[C:4]([O:13][CH3:14])=[C:3]([OH:15])[C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 38532555-Bromo-2-nitrovanillin

Product 1

HCID 14936539HCID 14936539, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To the mixture of phenol 154 (25.4 g, 92 mmol) in EtOH/H2O (350 mL/100 mL) were added FeSO47H2O (4.7 g) and Fe powder (47 g). The mixture was stirred at 100° C. for 1 hr. The mixture was cooled down to 50° C. and filtered to remove inorganic materials through celite. The filtrate was concentrated in vacuo to provide the title compound 155 (19.0 g, 84%).

Workup

  1. temperatureThe mixture was cooled down to 50° C.
  2. filtrationfiltered
  3. customto remove inorganic materials through celite
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cc3ea182e49c4681946e1de5b0ea1d13
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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