Tetrahydrofuran → 6-(2,6-Difluoro-4-(methoxymethyl)phenyl)-5-fluoropicolinic acid

HRID 1499583Notes

Reaction equation

HRID 1499583 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[N:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[CH:14][C:13]=1[F:22].C1COCC1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][C:13]=1[F:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70655699Methyl 6-(2,6-difluoro-4-(methoxymethyl)phenyl)-5-fluoropicolinate

Product 1

HCID 706549716-(2,6-Difluoro-4-(methoxymethyl)phenyl)-5-fluoropicolinic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methyl 6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxylate was treated with THF (2 mL), MeOH (2 mL) and 1.0 M aq. NaOH (2 mL, 2 mmol) at room temperature for 1 h. The volatile solvents were removed under reduced pressure. The residue was neutralized to pH around 5-6 with 1N HCl. The solids that precipitated were collected by filtration, rinsed with water, and dried to give the sub-title compound as a white solid (374 mg, 98.2%). LCMS calc. for C14H11F3NO3 (M+H)+ m/z=298.1. found: 298.0.

Workup

  1. customThe volatile solvents were removed under reduced pressure
  2. customThe solids that precipitated
  3. filtrationwere collected by filtration
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-954e2fc1ced84f809b0735d5018582cc
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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