Phosphorus oxychloride → 2177297-18-4

HRID 2264364Notes

Reaction equation

HRID 2264364 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[C:4]([F:10])[CH:3]=1.[CH:11]([NH:14][C:15](=O)[CH3:16])([CH3:13])[CH3:12].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:15](=[N:14][CH:11]([CH3:13])[CH3:12])[CH3:16])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 136874N-(1-Methylethyl)ethanamideHCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 674267372177297-18-4Yield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add TEA (10.05 mL) to a mixture of 4-bromo-2,6-difluoro-phenylamine (10.0 g), N-isopropyl acetamide (9.73 g), phosphoryl chloride (6.70 mL) in toluene (150 mL). Heat the mixture to reflux for 3 h. Cool the mixture and remove the solvent under vacuum. Dissolve the crude in DCM, wash with an aqueous saturated solution of sodium bicarbonate several times to remove all traces of acid. Dry over sodium sulfate and remove the solvent under vacuum to afford 14 g of the title compound. MS (ES+): m/z=292 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 3 h
  3. temperatureCool the mixture
  4. customremove the solvent under vacuum
  5. dissolutionDissolve the crude in DCM
  6. washwash with an aqueous saturated solution of sodium bicarbonate several times
  7. customto remove all traces of acid
  8. dry with materialDry over sodium sulfate
  9. customremove the solvent under vacuum

Sources & evidence

ORD record
ord-a60ff680a524485e82e4d18e7965283b
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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