Phosphorus oxychloride → 4-Chloro-2-(trifluoromethyl)pyrimidine

HRID 41356Notes

Reaction equation

HRID 41356 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7](O)[CH:6]=[CH:5][N:4]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516506HCID 178516506, compound

Product 1

HCID 152943694-Chloro-2-(trifluoromethyl)pyrimidine

Procedure

To 2-(trifluoromethyl)pyrimidin-4-ol (2 g, 12 mmol) was added POCl3 (15 mL). It was refluxed overnight. The solvent was removed. 1N NaOH was added to the reaction mixture slowly until pH=10. The mixture was extracted with DCM (3×80 mL). Combined DCM layer dried over Na2SO4 and taken to dryness. The crude product was vacuum distilled. 4-chloro-2(trifluoromethyl)pyrimidine was obtained as a clear oil. (94%). 1H NMR (400 MHz, DCM) δ: 7.60 (d, J=3 Hz, 1H), 8.80 (d, J=3 Hz, 1H),

Workup

  1. temperatureIt was refluxed overnight
  2. customThe solvent was removed
  3. addition1N NaOH was added to the reaction mixture slowly until pH=10
  4. extractionThe mixture was extracted with DCM (3×80 mL)
  5. dry with materialCombined DCM layer dried over Na2SO4
  6. distillationdistilled

Sources & evidence

ORD record
ord-f2e15707bd564309ab7cccc581dfe216
Source dataset
uspto-grants-2013_09
Patent number
US08530652B2

Reaction notes

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