Phosphorus oxychloride → HCID 15907523, compound

HRID 651400Notes

Reaction equation

HRID 651400 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]=1O.P(Cl)(Cl)([Cl:19])=O>CN(C=O)C>[Cl:19][C:3]1[C:2]([Br:1])=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15907522Ethyl 3-bromo-2-hydroxy-5-nitrobenzoate

Product 1

HCID 15907523HCID 15907523, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2.38 kg (8.2 mol) of ethyl 3-bromo-5-nitrosalicylate was dissolved in 3000 ml of DMF, followed by the dropwise addition of 1.26 kg of phosphorus oxychloride at room temperature. The obtained mixture was heated to 90° C. and then maintained at that temperature under heating for 10 hours. The obtained mixture was cooled and then concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate and the obtained solution was washed with water, dehydrated and concentrated under reduced pressure to give 2.25 kg of the title compound as a colorless oil.

Workup

  1. temperaturemaintained at that temperature
  2. temperatureunder heating for 10 hours
  3. temperatureThe obtained mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in ethyl acetate
  6. washthe obtained solution was washed with water
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff9851e420af433c9cf3fda914027666
Source dataset
uspto-grants-2001_08
Patent number
US06281214B1

Reaction notes

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