Phosphorus oxychloride → Methyl 3-(2-cyanophenyl)benzoate

HRID 399808Notes

Reaction equation

HRID 399808 reaction equation
CC1(C)CO[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[N:3]1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])#[N:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18945305Methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate

Product 1

HCID 1392768Methyl 3-(2-cyanophenyl)benzoateYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate (1.25 g) in pyridine (5 ml) at 7° C. was added dropwise phosphoryl chloride (0.75 ml) keeping the reaction temperature below 20° C. The reaction mixture was stirred at 100° C. for 4 hours. After being cooled to room temperature, the mixture was quenched by water, and the emulsion was extracted with ethyl acetate (50 ml). The organic layer was successively washed with 6N-hydrochloric acid and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (25 g) with dichloromethane as an eluent. The fractions containing the object compound were combined and evaporated in vacuo. The crystalline residue was recrystallized from methanol to afford methyl 3-(2-cyanophenyl)benzoate (0.7 g).

Workup

  1. customthe reaction temperature below 20° C
  2. temperatureAfter being cooled to room temperature
  3. customthe mixture was quenched by water
  4. extractionthe emulsion was extracted with ethyl acetate (50 ml)
  5. washThe organic layer was successively washed with 6N-hydrochloric acid and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (25 g) with dichloromethane as an eluent
  10. additionThe fractions containing the object compound
  11. customevaporated in vacuo
  12. customThe crystalline residue was recrystallized from methanol

Sources & evidence

ORD record
ord-aad2887442964d88b41ff19299751a6a
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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