Phosphorus pentachloride → HCID 13505373, compound

HRID 2372311Notes

Reaction equation

HRID 2372311 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[I:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:17][C:15]1[CH:14]=[CH:13][C:9]([C:10]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:9]=2)=[O:12])=[C:8]([I:7])[CH:16]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 1394524-Chloro-2-iodobenzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13505373HCID 13505373, compoundYield 164.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1.47 g of PCl5 (7.08 mmol, 1 eq.) in 35 mL of 1,2-dichloroethane was cooled to 0° under N2, then 2.00 g of 2-iodo-4-chlorobenzoic acid (7.08 mmol), 1 eq.) was added neat, at once. The bath was removed, the reaction allowed to warm to 25° and maintained there for 3 hr. The volatiles were removed in vacuo, the residue dissolved in 35 mL of fresh 1,2-chloroethane and again evaporated. The residual oil was dissolved in 70 mL of benzene, cooled to 0° and treated with 0.94g of AlCl3 (7.08 mmol, 1 eq.). After 1 hr at 0°, the reaction was allowed to warm to 25° and maintained there overnight. The mixture was poured onto 200 mL of ice, warmed and extracted with Et2O (3×100 mL). The combined Et2O layers were washed with saturated NaHCO3 (2×200 mL), saturated NaCl (1×300 mL), dried (MgSO4), and the solvents removed in vacuo to yield 2.00 g (82%) of 4-chloro-2-iodobenzophenone as a yellow oil.

Workup

  1. customThe bath was removed
  2. temperatureto warm to 25°
  3. temperaturemaintained there for 3 hr
  4. customThe volatiles were removed in vacuo
  5. dissolutionthe residue dissolved in 35 mL of fresh 1,2-chloroethane
  6. customagain evaporated
  7. dissolutionThe residual oil was dissolved in 70 mL of benzene
  8. temperaturecooled to 0°
  9. temperatureto warm to 25°
  10. temperaturemaintained there overnight
  11. temperaturewarmed
  12. extractionextracted with Et2O (3×100 mL)
  13. washThe combined Et2O layers were washed with saturated NaHCO3 (2×200 mL), saturated NaCl (1×300 mL)
  14. dry with materialdried (MgSO4)
  15. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-9beed6595a764593ad317dcdbe0170fd
Source dataset
uspto-grants-1992_03
Patent number
US05098901

Reaction notes

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