Trifluoroacetic acid → 5-(3-Fluorophenyl)picolinic acid

HRID 711243Notes

Reaction equation

HRID 711243 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16]C(C)(C)C)=[O:15])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67208627Tert-butyl 5-(3-fluorophenyl)picolinate

Product 1

HCID 463131255-(3-Fluorophenyl)picolinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 5-(3-fluorophenyl)picolinate 33-5 (414 mg, 1.51 mmol) in dichloromethane (3 mL) was added TFA (1.5 mL) dropwise at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was diluted with dichloromethane (100 mL) and H2O (100 mL), adjusted with Na2CO3 to pH around 4, and separated. The organic layer was washed with H2O and brine, dried over Na2SO4, concentrated to dryness to afford 5-(3-fluorophenyl)picolinic acid 6-7 as an off-white solid. MS m/z 218.1 (M+1)

Workup

  1. customseparated
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1f50d9ae574148c9b94259358edc1c31
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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