Sulfuric Acid → 2-Bromo-6-nitrophenol

HRID 2271426Notes

Reaction equation

HRID 2271426 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])([O-])=[O:7].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18]>O.C(OCC)(=O)C>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:6]([O-:9])=[O:7])[C:13]=1[OH:18]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 72442-BromophenolHCID 24268Sodium Nitrate

Product 1

HCID 135454532-Bromo-6-nitrophenolYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 60 mL of concentrated sulfuric acid diluted with 186 mL of water was cooled to room temperature. Sodium nitrate (79.2 g, 0.93 mol) was added to the solution. 2-Bromo-phenol 1a (60 mL, 0.52 mol) was added dropwise at such a rate that the reaction temperature was kept below 25° C. The reaction mixture was stirred at room temperature for 2 hours. The precipitate was dissolved in 320 mL of ethyl acetate. The mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2-bromo-6-nitro-phenol 1b (48.2 g, yield 42.8%) as a yellow solid.

Workup

  1. customwas kept below 25° C
  2. washThe mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-76cb03e5800c4acfa27bc43ecbc82368
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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