Hydrogen Peroxide → 5-Fluoro-3-nitrobenzene-1,2-diol

HRID 657012Notes

Reaction equation

HRID 657012 reaction equation
B(O)(O)O.[OH:5]O.S(=O)(=O)(O)O.[F:12][C:13]1[CH:14]=[C:15]([N+:23]([O-:25])=[O:24])[C:16]([OH:22])=[C:17](C(=O)C)[CH:18]=1>O1CCCC1.O>[F:12][C:13]1[CH:18]=[C:17]([OH:5])[C:16]([OH:22])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 27589845'-Fluoro-2'-hydroxy-3'-nitroacetophenone

Product 1

HCID 688163705-Fluoro-3-nitrobenzene-1,2-diolYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Boric acid (20.45 g, 330.7 mmol), and hydrogen peroxide (35%, 36.8 mL) in tetrahydrofuran (150 ml) was treated with concentrated sulfuric acid (15 ml) and the mixture was stirred at rt for 30 min. 1-(5-Fluoro-2-hydroxy-3-nitrophenyl)ethanone (15 g, 75.4 mmol) in tetrahydrofuran (45 ml) was added and reaction heated for 48 h at 75° C. The reaction mixture was cooled to rt, diluted with water and extracted with DCM (3×500 ml). The combined organic phases were dried on magnesium sulphate, evaporated and the residue was subjected to column chromatography on silica gel using a 20%-80% EtOAc: 40-60 petroleum ether gradient to provide the desired compound (6.55 g, 50%), a 5:1 mixture of desired product and 1-(5-fluoro-2-hydroxy-3-nitrophenyl)ethanone (4 g) and recovered 1-(5-fluoro-2-hydroxy-3-nitrophenyl)ethanone (1.5 g).

Workup

  1. customreaction
  2. temperatureheated for 48 h at 75° C
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionextracted with DCM (3×500 ml)
  5. customThe combined organic phases were dried on magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-5b28af1636194bb9b601142ea07d48ee
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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