Water → HCID 86590509, compound

HRID 1696897Notes

Reaction equation

HRID 1696897 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[Li].FC([I:19])(F)F.O>C1COCC1.C(OCC)C>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[C:7]([I:19])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 16843TrifluoroiodomethaneHCID 27336592,6-Dichloro-5-fluoronicotinic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 86590509HCID 86590509, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

A solution of 2,6-dichloro-5-fluoronicotinic acid (10 g) in THF (100 mL) at −78° C. was treated with 1.6M methyllithium in diethyl ether (62.5 mL), stirred at −25° C. for 1.5 hours, cooled to −78° C., treated with trifluoromethyl iodide (22.6 g) over 30 minutes, stirred at −78° C. for 1.5 hours, −25° C. for 1.5 hours, and 0° C. for two hours, treated with water, concentrated to remove the organic solvents, washed with diethyl ether, acidified with 1M HCl, and extracted with diethyl ether; and the extract was dried (Na2SO4), filtered, and concentrated.

Workup

  1. temperaturecooled to −78° C.
  2. stirringstirred at −78° C. for 1.5 hours, −25° C. for 1.5 hours
  3. wait0° C. for two hours
  4. concentrationconcentrated
  5. customto remove the organic solvents
  6. washwashed with diethyl ether
  7. extractionextracted with diethyl ether
  8. dry with materialand the extract was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c47f0a2fc72a4af9a6087802bd2fde97
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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