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

HRID 1494335Notes

Reaction equation

HRID 1494335 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([O:16][CH3:17])[CH:10]=[CH:9]2.S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([N+:1]([O-:4])=[O:2])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 220971876-Bromo-2-methoxy-1-nitronaphthaleneYield 81.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

An ice-cooled solution of 100% nitric acid (12.0 ml, 0.27 mol) in 95 ml of acetic anhydride was added dropwise to a solution of 6-bromo-2-methoxynaphthalene (61.7 g, 0.26 mol) and 0.25 ml of conc. sulfuric acid in 570 ml of acetic anhydride while maintaining the temperature at +30° to +40° C. The mixture was stirred for an additional 10 min. and filtered. The solid was washed with water and dried to give 60.0 g (73%) of the nitro compound. M.p. 151-152° C., 1H-NMR (CDCl3): 3.98 (s, 3H, CH3), 7.16-7.93 (m, 5H, ArH).

Workup

  1. temperaturewhile maintaining the temperature at +30° to +40° C
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-4d4eb6745b824dc3a747cb868020966a
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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