Nitric Acid → 5-bromo-3,4-dihydro-8-nitro-2H-naphthalen-1-one

HRID 2114543Notes

Reaction equation

HRID 2114543 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:16].[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:15]=[CH:14][C:13]([N+:1]([O-:4])=[O:2])=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 108895725-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 199907905-bromo-3,4-dihydro-8-nitro-2H-naphthalen-1-oneYield 336.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To prepare this compound, 90% fuming nitric acid (0.115 gram, 0.165 mmol) was added to a solution of 5-bromo-3,4-dihydro-2H-naphthalen-1-one (0.34 g, 1.50 mmol) in 3 mL concentrated sulfuric acid at 0° C. After 45 minutes, the mixture was poured into ice, and 6 N aqueous sodium hydroxide (9 mL) was added very slowly. That mixture was extracted twice with EtOAc (40 mL each), and the two extracts were combined. The combined EtOAc extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was subjected to flash chromatography (40% EtOAc/hexanes) and recrystallization (EtOAc/hexanes) to afford 0.15 g (38%) of 5-bromo-3,4-dihydro-8-nitro-2H-naphthalen-1-one. 1H NMR (500 MHz, CDCl3) δ 7.84 (d, J=8.2, 1H), 7.25 (d, J=8.2, 1H), 3.07 (t, J=6.2, 2H), 2.74 (t, J=6.7, 2H), 2.18-2.25 (m, 2H).

Workup

  1. additionwas added very slowly
  2. extractionThat mixture was extracted twice with EtOAc (40 mL each)
  3. extractionThe combined EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was subjected to flash chromatography (40% EtOAc/hexanes) and recrystallization (EtOAc/hexanes)

Sources & evidence

ORD record
ord-08e268109c4b48ce85098d2562fe0388
Source dataset
uspto-grants-2008_10
Patent number
US07435733B2

Reaction notes

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