Acetic Acid → 2-Bromo-7-nitronaphthalene

HRID 891961Notes

Reaction equation

HRID 891961 reaction equation
N([O-])=O.[Na+].C(O)(=O)C.N[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17]2)=[CH:12][CH:11]=1.[BrH:23]>S(=O)(=O)(O)O>[Br:23][C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][CH:14]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 154071007-Nitro-2-aminonaphthaleneHCID 23668193Sodium Nitrite

Product 1

HCID 8259512-Bromo-7-nitronaphthaleneYield 51%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of NaNO2 (1.1 g, 24 mmol) in sulfuric acid (8.4 ml) was added at 0° C. acetic acid (8.9 ml) and 7-amino-2-nitro-naphthalene (2.1 g, 1mmol). This solution was added to a suspension of CuBr (2.5 g, 39 mmol) in conc. HBr (16 ml) at 0° C. and the mixture was stirred for 1 hour. The mixture was poured on ice and the aqueous phase was extracted with methylene chloride. The crude product was purified by chromatography to give 1.9 g (7.4 mmol, 51%) of the title compound, MS: m/e=251.2 (M+).

Workup

  1. additionThe mixture was poured on ice
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-5e6a2815260449169d9b160b38b13ab0
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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