Nitric Acid → 6-Bromo-2-methoxy-1-nitronaphthalene

HRID 1751625Notes

Reaction equation

HRID 1751625 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N+:14]([O-:16])=[O:15])=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 220971876-Bromo-2-methoxy-1-nitronaphthaleneYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Bromo-6-methoxynaphthalene (20 g, 84.4 mmol) was dissolved in acetic acid (140 mL) by stirring vigorously at 70° C. This solution was cooled to 50° C. and a solution of nitric acid (>90%, 4 mL) in acetic acid (28 mL) was added dropwise. The resulting reaction mixture was stirred at 50° C. for four hours and then cooled to room temperature. The yellow solid was isolated by filtration and recrystallized from acetic acid to yield 6-bromo-2-methoxy-1-nitronaphthalene (18.7 g, 76% yield).

Workup

  1. temperatureThis solution was cooled to 50° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 50° C. for four hours
  4. temperaturecooled to room temperature
  5. customThe yellow solid was isolated by filtration
  6. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-462f677311ca4b118a9b0b5653e9e4ea
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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