Phosphorus oxychloride → HCID 86708578, compound

HRID 921703Notes

Reaction equation

HRID 921703 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([Br:17])[C:15]=1[Cl:16])[C:10]([NH2:12])=O>C(#N)C>[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([Br:17])[C:15]=1[Cl:16])[C:10]#[N:12]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86708579HCID 86708579, compound

Product 1

HCID 86708578HCID 86708578, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(328B1): Phosphoryl trichloride (90 ml, 966 mmol) was added to a suspension of 3,5-dibromo-4-chlorobenzamide (148 g, crude, ˜380 mmol) in acetonitrile (1500 ml) at reflux. The reaction mixture was heated to reflux for additional 90 minutes. The reaction mixture was evaporated to dryness, and then partitioned between EtOAc and aq. NaHCO3 solution. The organic layer was washed one more time with aq. NaHCO3 solution, once with brine, then dried over MgSO4, filtered and evaporated to dryness to give 3,5-dibromo-4-chlorobenzonitrile (110 g). The material was used without further purification in the next reaction.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for additional 90 minutes
  4. customThe reaction mixture was evaporated to dryness
  5. custompartitioned between EtOAc and aq. NaHCO3 solution
  6. washThe organic layer was washed one more time with aq. NaHCO3 solution
  7. dry with materialonce with brine, then dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-bbd2db9defc545f7a75ef86b6c249885
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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