Sulfuric Acid → 3-Bromo-5-nitrophenol

HRID 1941972Notes

Reaction equation

HRID 1941972 reaction equation
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].OS(O)(=O)=O.N([O-])=O.[Na+]>CCO.O>[Br:8][C:7]1[CH:2]=[C:3]([OH:12])[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 49766558HCID 49766558, compound

Product 1

HCID 104889843-Bromo-5-nitrophenolYield 82.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To an ice-cold solution of 2-amino-3-bromo-5-nitro-phenol (6.50 g, 27.89 mmol) in EtOH (150.0 mL) was added concentrated H2SO4 (9.40 mL, 177.13 mmol) portion wise. The reaction mixture was then heated to 50° C. followed by portion wise addition of NaNO2 (6.19 g, 89.82 mmol). The resulting solution was refluxed at 80° C. for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc (3×150.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified over silica gel (100-200 M, 10% EtOAc-Hexane) to get the desired product (5.0 g, 82%).

Workup

  1. temperatureThe resulting solution was refluxed at 80° C. for 2 h
  2. extractionextracted with EtOAc (3×150.0 mL)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified over silica gel (100-200 M, 10% EtOAc-Hexane)

Sources & evidence

ORD record
ord-ff5bc5a6d2a047ba920238c8c2ef2d71
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

Loading…