Water → 1,3-Difluoro-2-nitrobenzene

HRID 2110352Notes

Reaction equation

HRID 2110352 reaction equation
B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[F:10][C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:12]=1[NH2:13].O>C(O)(=O)C>[F:10][C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:12]=1[N+:13]([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 796472,6-DifluoroanilineHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 879221,3-Difluoro-2-nitrobenzeneYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80° C. 2,6-Difluoroaniline (11.0 g, 85 mmol) in glacial acetic acid (50 mL) was added slowly to the mixture. The temperature was maintained between 80-90° C. for 1 hour. The cooled reaction mixture was poured into water and extracted twice with diethyl ether. The combined organic layers were washed with a dilute solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified via Biotage chromatography (FlasH90i, silica, 10% THF/hexane) and the product washed with hexane to afford 2,6-difluoronitrobenzene (7.0 g) (52%). MS (ESI) m/z 160 ([M+H]+).

Workup

  1. temperatureThe temperature was maintained between 80-90° C. for 1 hour
  2. customThe cooled reaction mixture
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic layers were washed with a dilute solution of sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified via Biotage chromatography (FlasH90i, silica, 10% THF/hexane)
  8. washthe product washed with hexane

Sources & evidence

ORD record
ord-3c3bdff39bf74c9089441df7710229a7
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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