Acetic Acid → 4-Bromo-5-nitroveratrole

HRID 1691843Notes

Reaction equation

HRID 1691843 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13].C(O)(=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 1709684-Bromo-5-nitroveratroleYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Following the procedure of J. Org. Chem. 1960, 25, 721) 4-Bromoveratrole (16.28 g, 75.0 mmol) was slowly added to a stirred solution of concentrated nitric acid (122 ml) and acetic acid (365 ml) maintained at 10° C. The reaction mixture was stirred at 15° C. for one hour, then was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from ethanol to give 1-bromo-4,5-dimethoxy-2-nitro-benzene (13.144 g, 66.9%) as yellow crystals.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-4a5fcc22681b45cba193ca367bba4a46
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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