Water → 5-Bromo-2-nitrovanillin

HRID 576381Notes

Reaction equation

HRID 576381 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].[Br:15]Br.O>CC(O)=O.II>[Br:15][C:9]1[C:2]([OH:1])=[C:3]([O:13][CH3:14])[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH:8]=1)[CH:6]=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

Product 1

HCID 38532555-Bromo-2-nitrovanillinYield 98%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 176Acetic AcidSolvent

Procedure

To the mixture of aldehyde 153 (28.0 g, 142 mmol) and I2 (1.5 g) in AcOH (160 mL) was added Br2 (8.0 mL, 157 mmol) at 0° C. The mixture was warmed up to r.t. and stirred at r.t. for 15 hours. The mixture was poured into water (2.0 L) with stirring. The mixture was stirred at r.t. for 30 min. The mixture was extracted with EtOAc (1 LX2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the compound 154 (38 g, 98%).

Workup

  1. stirringwith stirring
  2. stirringThe mixture was stirred at r.t. for 30 min
  3. extractionThe mixture was extracted with EtOAc (1 LX2)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00910c903c404459bf4395918d05e588
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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