Water → Phenol, 4-chloro-2,6-dinitro-

HRID 1824709Notes

Reaction equation

HRID 1824709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.F[B-](F)(F)F.[O:17]=[N+:18]=[O:19].O>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:18]([O-:19])=[O:17])[C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69804-Chloro-2-nitrophenolHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 6952Phenol, 4-chloro-2,6-dinitro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-chloro-2-nitrophenol (4 g, 23 mmol) in acetonitrile (100 ml) was cooled to −25 C.°, and gradually added with nitronium tetrafluoroborate powder (4.9 g). The reaction mixture was stirred for 2 hours while the temperature was raised to −10 C.°, and the reaction was stopped by adding 10 ml of water. The acetonitrile was evaporated under reduced pressure, and the residue was diluted with diethyl ether. The ether layer was washed with water, then washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated by vacuum concentration to obtain the title compound as yellow plate crystals (5.1 g).

Workup

  1. temperaturewas raised to −10 C.°
  2. customThe acetonitrile was evaporated under reduced pressure
  3. additionthe residue was diluted with diethyl ether
  4. washThe ether layer was washed with water
  5. washwashed twice with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated by vacuum concentration

Sources & evidence

ORD record
ord-92716d8e172c411ba31aa45db3065f5c
Source dataset
uspto-grants-2006_05
Patent number
US07045516B1

Reaction notes

Loading…