Phosphorus oxychloride → 2-Chloro-5-fluoro-1,3-dinitrobenzene

HRID 2235543Notes

Reaction equation

HRID 2235543 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](O)=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.P(Cl)(Cl)([Cl:17])=O>CN(C)C=O>[Cl:17][C:5]1[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 94951Phenol, 4-fluoro-2,6-dinitro-

Product 1

HCID 123611032-Chloro-5-fluoro-1,3-dinitrobenzeneYield 278.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.65 g (2.2 mmol) of 4-fluoro-2,6-dinitrophenol in 30 mL dimethylformamide was added 1.4 mL (15 mmol) of phosphorous oxychloride. The mixture was heated to 70° C. overnight, cooled to room temperature and quenched with ice. The mixture was diluted with water and the precipitate was collected giving 1.35 g (82%) of the title compound as a cream colored solid.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with ice
  3. additionThe mixture was diluted with water
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-0ceec7ef6fca4d02b7ab6de3873247d3
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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