Sodium Nitrate → 2-Bromo-4-fluoro-6-nitrophenol

HRID 384291Notes

Reaction equation

HRID 384291 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[N+:10]([O-])([O-:12])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[OH:9]

Participants

5

Reactant 2

HCID 24268Sodium NitrateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 27733842-Bromo-4-fluoro-6-nitrophenolYield 80.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

2-Bromo-4-fluoro-phenol 2a (8.0 g, 41.9 mmol) was dissolved in 10 mL of sulfuric acid (50%) followed by addition of a solution of sodium nitrate (7.1 g, 83.5 mmol) in 24 mL of sulfuric acid (25%), upon cooling by an ice-water bath. The reaction mixture was reacted at room temperature for 1.5 hours and the reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 50 mL of water and extracted with ethyl acetate (50 mL×2). The combined organic extracts were washed with water and saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2-bromo-4-fluoro-6-nitro-phenol 2b (8.0 g, yield 80.8%) as a red solid, which was directly used in the next step.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThe reaction mixture was reacted at room temperature for 1.5 hours
  3. extractionextracted with ethyl acetate (50 mL×2)
  4. washThe combined organic extracts were washed with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fce099ad4064986893b3639597284ec
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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