Phosphorus oxychloride → 2-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole

HRID 479130Notes

Reaction equation

HRID 479130 reaction equation
[CH3:1][C:2]1[N+:3]([O-])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[O:5][C:6]=1[CH3:7].O=P(Cl)(Cl)[Cl:21]>C(Cl)Cl>[Cl:21][CH2:1][C:2]1[N:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[O:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10515280Oxazole, 4,5-dimethyl-2-[4-(trifluoromethyl)phenyl]-, 3-oxide

Product 1

HCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18.5 g of the above prepared 4,5-dimethyl-2-(4-trifluoromethyl-phenyl)-oxazole 3-oxide (72 mmol) was dissolved in 250 ml of CH2Cl2 and treated with 7.909 ml of POCl3 (86.4 mmol). The reaction mixture was refluxed over night and then quenched by carefully pouring onto crashed ice/3N NaOH. Separation of the layers, additional extraction of the aqueous phase with CH2Cl2 and drying of the combined organic layers over magnesium sulfate left, after evaporation of the solvents, 19.78 g of crude product as light brown crystals, which was used as such for the next step.

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. customquenched
  3. additionby carefully pouring
  4. customSeparation of the layers, additional extraction of the aqueous phase with CH2Cl2
  5. dry with materialdrying of the combined organic layers over magnesium sulfate
  6. waitleft
  7. customafter evaporation of the solvents, 19.78 g of crude product as light brown crystals, which

Sources & evidence

ORD record
ord-9db056811bf64bd0867c42733b82fe7e
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…