Sulfuric Acid → 2-Bromo-6-nitrophenol

HRID 384284Notes

Reaction equation

HRID 384284 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, 0.932 mol) was added to the solution. 2-Bromo-phenol 1a (60 mL, 0.516 mol) was added dropwise at such a rate that the reaction temperature was kept below 25° C. The reaction mixture was reacted at room temperature for 2 hours and monitored by thin layer chromatography (TLC) until the disappearance of the starting materials. The precipitate was dissolved in 320 mL of ethyl acetate. The mixture was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and 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. customThe reaction mixture was reacted at room temperature for 2 hours
  3. washThe mixture was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f68c7208a9734e78a0d3df22207b622b
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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