Phosphorus oxychloride → HCID 23537174, compound

HRID 1791238Notes

Reaction equation

HRID 1791238 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[C:10](O)=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[N:7][CH:6]=1)[CH3:2].O=P(Cl)(Cl)[Cl:25]>>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[C:10]([Cl:25])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[N:7][CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469734HCID 178469734, compound

Product 1

HCID 23537174HCID 23537174, compound

Procedure

Heat a mixture of 4-Hydroxy-6-(2-trifluoromethyl-phenyl)-nicotinic acid ethyl ester (9.0 g, 0.029 mol) in POCl3 (22 g) at 110° C. for 2 hours. Evaporate the POCl3, and add ice (100 g) followed by careful addition of saturated NaHCO3. Extract with EtOAc, dry (MgSO4), and evaporate to provide 4-chloro-6-(2-trifluoromethyl-phenyl)-nicotinic acid ethyl ester as a brown oil.

Workup

  1. temperatureHeat
  2. customEvaporate the POCl3
  3. additionadd ice (100 g)
  4. additionfollowed by careful addition of saturated NaHCO3
  5. extractionExtract with EtOAc
  6. dry with materialdry (MgSO4)
  7. customevaporate

Sources & evidence

ORD record
ord-3838968a21b64ac69cc878ec3d8ac56a
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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