2,6-Lutidine → 2,6-Bis(trifluoromethyl)-3-methoxycarbonyl-4-chloropyridine

HRID 542115Notes

Reaction equation

HRID 542115 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7](O)[CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1.N1C(C)=CC=CC=1C.O=P(Cl)(Cl)[Cl:30]>>[F:1][C:2]([F:19])([F:18])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([Cl:30])[CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178498966Methyl 2,6-bis(trifluoromethyl)-4-hydroxy-3-pyridinecarboxylate

Product 1

HCID 138828782,6-Bis(trifluoromethyl)-3-methoxycarbonyl-4-chloropyridineYield 19.7%

Procedure

A mixture of 6.7 g (0.0232 mol) of product of Example 4, 2.8 g (0.026 mol) of 2,6-lutidine, and 50 ml of POCl3 was held at reflux for 18 hours and concentrated. The residue was treated with water and extracted with ether. The ether extract was washed with 10% NaOH and then with saturated NaCl, dried, and concentrated. The residue was kugelrohr distilled at 133 Pa (pot temperature 90° C.). The distillate was recrystallized from hexane at low temperature to give 1.4 g (19.7%) of product; mp 48°-49° C.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. additionThe residue was treated with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with 10% NaOH
  7. dry with materialwith saturated NaCl, dried
  8. concentrationconcentrated
  9. distillationThe residue was kugelrohr distilled at 133 Pa (pot temperature 90° C.)
  10. customThe distillate was recrystallized from hexane at low temperature

Sources & evidence

ORD record
ord-e3e49325bc584731ad8b270fd87a4e03
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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